Conceptsoforganicchemistryvol I

Copyright © 2016 by Ajnish Gupta
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(i)
Preface
The guiding principle in writing this book was to create a textbook for students- a textbook
that presents the material in a way that they learn to solve all the questions along with
the strategy to approach the problems.
In this book we mixed all our teaching experience of 12 years along with theoratical and
experimental knowledge to generate a hand book for all students to reason their way to a
solution rather than memorize a multitude of facts, hoping they don’t run out of memory.
This book covers mainly 4 units with 61 se ctions w hich a re real tools of Organic
chemistry, which a students must know before dealing any chemical reactions.
Organic chemistry is very easy and conceptual subject and need proper understanding of
the basics and stretegy to solve the questions in corret manner.
This book will prepare your right mindset for learning Organic Chemistry. This mindset is
essentially the one that focuses you on a small number of straight forward, repeated, fun-
damental concepts and helps you to apply them in different ways to solve the variety of
problems you face in organic chemistry.
This book is complete as it not only covers theory in proper sequence but also provide
varieties of questions along with 10 test papers to judge your knowledge before going to
start chemical reactions.
This book also covers all the questions of AIEEE, IIT-Mains, IIT-Advanced, AIPMT & other
medical exams from 2000 to 2016.
In this book balance has to be achieved between the number of questions and the quality of
the questions, especia lly because it is relatively easy to frame a very la rge number of
multiple-choice questions and theory of the subject.
The questions in this book have been selected keeping three things in mind.
First- the questions are such that they really test the understanding of the subject.
Second- the questions cover all concepts.
Third- the number of questions has been kept large enough to offer meaningful practice to
the students.
We would like to thank the editors and production staff for their efforts in bringing out the
book. Suggestions from readers for the improvement of the book are welcome.
Ajnish Kumar Gupta & Bharti Gupta
Ajnish@OrganicChemistry.co.in
9122057123
(ii)
Acknowledgement
We are thankful to all the teachers who taught us during the concept building session of
our life specially Dr. Nizamuddin sir, senior Chandra Vijay Rao and Dr. Vijay Pratima
Mittal madam.
We have written this book to remove the fever of organic chemistry from mind of students.
We particularly want to thank many wonderful and talented students whom we have
taught over the years who in turn taught us how to be a good teacher and how we can
help others.
We wa nt to make this book as user friendly as possible, and we will appreciate any
comments that will help us to achieve this goal in future editions.
Finally, this edition has been presented before you with efforts to make it error free. Any
that remain are our responsibility; if you find any, please let us know so they can be
corrected in future printing.
Ajnish Gupta & Bharti Gupta

Ajnish@OrganicChemistry.co.in
Contact@CoachMe.co.in
09122057123
(iii)
Table of Contents
Page No.
Unit 1 : Basic understanding of organic chemistry 01
Section 01 : Introduction of organic chemistry 02
Section 02 : What is organic chemistry 04
Section 03 : Representation of organic compounds 06
Section 04 : Reason for the formation of large number of organic compounds 10
Section 05 : Functional groups 12
Section 06 : Homologue & Homologous series 16
Section 07 : Nature of C, H & functional groups 19
Section 08 : Saturated & Unsaturated molecules with important points 22
Section 09 : Hybridization 25
Section 10 : Classification of organic compounds 28
Section 11 : Baeyer’s strain theory 31
Exercise 1 : Subjective approach 33
Answer : Subjective approach 39
Exercise 2 : Objective approach 48
Exercise 3 : World of competition 56
Answer : Objective approach 59
Answer : World of competition 60
Approach : Objective approach (Exercise-2) 61
Approach : World of competition (Exercise-3) 64
Unit 2 : Nomenclature of organic compounds 66
Section 01 : Alkyl groups 67
Section 02 : Basic concept of IUPAC nomenclature 69
Section 03 : Points to write IUPAC nomenclature 72
Section 04 : Points to write IUPAC nomenclature for multiple bonds & rings 76
Section 05 : Points to write IUPAC nomenclature of compounds with functional groups 80
Section 06 : Nomenclature of Bicyclic & Spiro compounds 85
Section 07 : Some common names commonly used in organic chemistry 87
Section 08 : Degree of unsaturation 103
Section 09 : Chemically different hydrogen 106
(iv)
Test 1 : Basic understanding of organic chemistry & nomenclature 156
Answer : Test- 1, 2, 3 172
Approach : Test paper 1 173
Unit 3 : Study of isomerism 179
Section 01 : Basic concept of isomerism 180
Section 02 : Chain isomerism 182
Section 03 : Positional isomerism 184
Section 04 : Functional isomerism 186
Section 05 : Metamerism 188
Section 06 : Basic concept of tautomerism 193
Section 07 : % enol content 197
Section 08 : Types of tautomerism 200
Section 09 : Basic concept of geometrical isomerism 201
Section 10 : Nomenclature used in geometrical isomerism 204
Section 11 : Basic concept of optical isomerism 207
Section 12 : Nomenclature used in optical isomerism 211
Section 13 : Terms used in optical isomerism 215
Section 14 : Compound showing optical isomerism along with calculation of number
of stereoisomers 218
Section 15 : Conformational isomerism 221
Section 16 : Conformation of cyclohexane 226
Section 17 : Interconversion of one form of molecule into another 230
Section 18 : Finding relationship between pair of compounds 232
Section 19 : Physical properties of organic compounds 236
(v)
Test 4 : Concept of isomerism 297
Answer : Test- 4, 5, 6 314
Unit 4 : Electronic effect & it’s application 321
Section 01 : General concept of organic reactions 322
Section 02 : Inductive effect 326
Section 03 : Basic concept of resonance 328
Section 04 : Points to draw resonating structures 331
Section 05 : points to check stability of resonating structures 334
Section 06 : Mesomeric effect 337
Section 07 : Hyperconjugation 339
Section 08 : Electromeric effect 341
Section 09 : Organic reaction intermediates 343
Section 10 : Carbocations 345
Section 11 : Stability of carbocation 347
Section 12 : Rearrangement of carbocations 349
Section 13 : Classification of carbocation 354
Section 14 : Carbanions 356
Section 15 : Free radical 359
Section 16 : Carbenes 363
Section 17 : Nitrene 365
Section 18 : Benzyne 367
Section 19 : Ajnish rule & It’s application in organic chemistry 369
Section 20 : General concept of Acid & Base 375
Section 21 : Concept to decide relative acidic strength 378
Section 22 : Concept to decide relative basic strength 381
(vi)
Test 7 : Electronic effect & it’s application 485
Answer : Test- 7, 8, 9 502
Test 10 : Tools of organic chemistry 503
Test 10 : Answer 508

(vii)
Basic understanding of organic chemistry
Unit
1
Basic understanding of Organic Chemistry
This unit is designed to lay the foundation for your organic chemistry. Here you will learn what is
organic chemistry, how organic compounds are represented, what is the reason for forma tion of large
number of organic compounds, functional groups, homologues, nature of carbon & hydrogen, saturation
and unsaturation, hybridization, classification of organic compounds and Baeyer’s strain theory.
We wrote this book for one simple reason : We love writing. We get great
pleasure and satisfaction from taking a complicated subject, turning it around
until we see it clearly from a new angle, and then explaining it in simple
words. We write to explain chemistry to students today the wa y we wish it
had been explained to us years ago.
 
Learning is easy at www.CoachMe.co.in 1

Section
1
Introduction of Organic Chemistry
Have you ever thought that when you read anything from “ any book” your eyes use an organic
compound (retinal) to convert visible light into nerve impulses. When you pick up this book from any
place, your muscles do chemical reactions on sugars to give you energy. As you read the words and
sentences of this book, gaps between your brain cells are being bridged by simple orga nic molecules
(neurotransmitter amines) so that nerve impulse can be passed around your brain and you can understand
all matters correctly and you did all that without consciously thinking about it.
You do not yet understand these processes in your mind but you are regularly carrying them out
in your bra in & body.
H 3C CH 3 CH 3
HO
CH 3H 3 C N NH2
11-Cis retinal H O H
Serotonin
(Absorbs light when we see) (Human neurotransmitter)
You are not alone there.........
 
No organic chemist, is so brilliant who can understand the detailed chemical working of human
mind or body very well.
So don’t be sad and give a smile to yourself so that your journey should be cheerful....
You do at least one thing after reading this page “Think the importance of organic chemistry and try
to search at least one thing which ma kes your life easy but not made of CARBON”.
?
?
 Are you thinking of this book, which you are reading presently - Made up of cellulose and
indeed carbon
 Notice board, Black or white board of schools - Made up of wood and indeed carbon.
 Cloths which you are wearing - Polyester, tericot, silk etc. - Polymer of organic compounds
 Perfumes, which you are using for good smell - Again organic molecule such as cis-jasmone
from jasmine flower and damascenone in smell of rose.
2 Learning is easy at www.CoachMe.co.in

 Medicines at the time of your sickness - Made up of organic compounds such as paracetamol
and aspirin
 Sugars to make your life sweet - Made up of glucose, sucrose and indeed carbon.
 Are you thinking for opposite sex attraction- Pheromones & hormones are responsible for it, which
are again made up of carbon.
 Are you now thinking for drugs - Then they are again organic and made up of carbon such as
cocaine, nicotine, etc.
 Polythene which are used to carry things - made up of ethene which indeed is made up of
carbon
 Blue jeans, which you are w earing - made up of indigo dyes, made up of carbon.
 Petrol or diesel- Again made up of carbon
 Candles for your birthda ys and parties for light - Again made up of carbon
 Are you thinking for bigger molecules such as Vitamins, Proteins, DNA, RNA – they are again
organic and made up of carbon.
 Trees, plants, flowers - They too are made up of carbon
 You, I or any human being along with all animals & plants- has some sort of carbon, in one
form or another.
O HO
MeOOC H 3C CH 3 O
HO O
N CH 3
H3 C O
CH 3 HO OH
Cocaine O
Damascenone-The smell of rose Vitamin C
O CH 3 O
OH
HO O O CH3
HO OH COOH
CH 3 OH
Cis Jasmone of jasmine Glucose Aspirin
CH3 CH 3
NH 2 O
 
H3 C CH 3 OH N N NH
N
HN N HN N NH 2
CH 3 Vitamin A Adenine Guanine
O NH 2 O O
HN H3 C
N NH NH
NH N O N O N O
O H H H
Indigo dye for blue colour Cytocine Uracil Thymine
Anything more which you want to suggest....
Examples may varies from yours to our’s but from these example we want to give a clear cut picture
of importance of organic chemistry and its applications in daily life i.e. everything around us are organic
in nature so
Love organic, feel organic and give a smile for organic....


Section
2 What is Organic Chemistry
What is Organic chemistry?

Why do so many people study it?
And why should I study it?
The answer to these questions is all around you. Every living organism is made up of organic
compounds. The proteins that make your hair, skin and muscles; the DNA that controls your genetic
heritage; the food that nourish you; the clothes that keep you warm and the medicines that heal you, are
all organic chemicals. Anyone with a curiosity about life and living things must have a basic understanding
of organic chemistry.
The foundation of organic chemistry dates from the mid 1700 s, when chemistry was evolving from
alchemist’s art into a modern science. At that time unexplainable differences were noted between
substances obtained from living sources and those obtained from mineral sources. Compounds obtained
from plants and animals were often difficult to isolate, purify and even difficult to work. The Swedish
chemist Torbern Bergman in 1770 was the first to differentiate “organic” and “inorganic” substances
and the term organic chemistry soon came to mean the chemistry of compounds found in living organism.
To many chemists at that time the only explanation for the differences in behavior of organic and
inorganic compound was that the organic compounds must contain a peculiar “vital force” as a result of
 
their origin in living substance. Due to this vital force theory chemist believed that organic compounds
could not be prepared and manipulated in the laboratory, as could inorganic compounds.
In 1816, how ever this vital force theory received a heavy blow when Michel Chevreul found that
soap, prepared by the reaction of alka li with animal fatcould be separated into several pure organic
compounds,which he termed “fatty acid”. For the first time, one organic substance (fat) was converted
into other organic substances (fatty acids and glycerin).
Animal fat NaOH Soap + Glycerin

H O 2
+
H 3O
soap Fatty acid
In 1828, vital force theory again got a heavy blow when Friedrich Wöhler prepared organic compound
urea, of human urine from inorganic compound ammonium cyanate.
Heat
NH 4 – OCN  NH 2CONH 2

Ammonium Cyanate Urea

By the mid of 1800s, the weight of evidence was clearly against the vital force theory which led
William Brande in 1848 to write “No definite line can be drawn between organic and inorganic
chemistry......... Any distinction........ Must for the present be merely considered as matters of practical
convenience calculated to further the progress of students”.
Chemistry toda y is unified. The same principles that explain the simplest inorganic compounds
also explain the most complex organic ones. The only distinguishing characteristic of organic chemistry
is that all contains the element carbon. Nevertheless, the division between organic and inorganic chemistry,
which began for historical reasons, maintains its practical convenience... to further the progress of students.
So, in general
“Organic chemistry is a branch of chemistry which deals with carbon and its compounds”
Atomic number
–number of electrons
6
C 12
–number of protons
Symbol
Atomic mass
From the periodic table we can easily find that it comprises of seven periods and eighteen groups.
First and second groups elements are called as s block elements, thirteen to eighteen group elements are
called p block elements, third to twelve group elements are d block while La to Lr w hich are downside
are called as f block elements.
When we carefully analyze the periodic table, it is clear that position of carbon is in second period
and fourteenth group and carbon is a non-metal.
Carbon is the basic element for life but it forms its compounds by combination with other elements
such as H, N, O, F, Cl, Br, I, S, P etc.
In Organic chemistry we mainly deal with
 Structural determination – How to find out the structures of new compounds, even if they are
available only in invisibly sma ll amount.
 Theoretical organic chemistry – How to understand those structures in terms of atoms and the
electrons that binds them together.
 Reaction me chanism – How to find out how those molecules reacts with each other and to
predict their reactions.
 Biological chemistry – How to find out what nature does and how the structures of biologically
 
active molecules are related to what they do.


Section
3
Representation of Organic Compounds
Organic chemistry is the study of compounds that contain carbon but there are some other elements
too associated with it such as H, O, and N. We know that carbon is tetravalent in nature and form
covalent compounds by sharing of electrons by generally H, F, Cl, Br, I, N, O, S and P. For sake of
simplicity all halogens are generally represented by X. In the study of molecules, you will notice that
oxygen has two covalent bonds, nitrogen has three covalent bonds and carbon has four covalent bonds
when they are neutral. Neutral hydrogen & halogens each have one covalent bond. If atoms have more
bonds or few er bonds than the number required for neutral molecule then they would have either a
formal charge or an unpaired electron. These numbers are very much important to remember when you
are first drawing structures of organic compounds because they provide a quick way to recognize when
you have made a mistake.
C N O H F Cl Br I X
This covalent bond may be of sigma (  )or pi (  ). Sigma bond is formed by lateral overlapping of
orbitals. It may be of s-s, s-p or p-p but pi bonds are formed by sidewise overlapping of p-p orbitals in
terms of organic chemistry.
 
+
s s s-s overlap
s p s-p overlap
yx yx
z+ z
p orbital p orbital p-p overlap along
the orbital axis
y y yy
Py Py p-p sideways overlap

As sigma bonds are strong as compared to pi bonds so generally pi bonds are involved in chemical
reaction with reagent, if present in molecule. When we compare the bond strength of bonds formed by
s-p & p-p overlapping; p-p bond is stronger so generally s-p bond break on treatment with suitable
reagent, such as in case of alkanes.
Organic chemistry concerns itself with the way in which these atoms are bonded together into stable
molecular structures and the way in which these structures change during chemical reactions.
For this organic molecules are represented by several ways
1. Lewis structure or dot structure –Here valence electrons in a molecule are represented as dots.
When you draw Lewis structure you must make sure that hydrogen atom is surrounded by no
more than two electrons, and C, O, N and halogen (F, Cl, Br, I) atoms are surrounded by no more
than eight electrons. In other words, they must obey the octet rule. The valence electrons not
used in bonding are called as non-bonding electrons or lone pair of electrons. Lewis structures
are useful because they show us which atoms are bonded together and tell us whether any atom
possess lone pair of electrons or have a formal charge.
....
H
HCH
H
.... .
HCO H
H H
2. Dash structure or Kekule structure–In this representation, dash represents the bonds. Single
dash represents a single bond, double dash is used for double bond of any type such as of C=C,
C=N, C=S etc. and triple dash represent triple bond of any type such as C  C or C  N, etc. In this
representation lone pair of electrons of hetero atoms (O, N, S, and P etc.) may or may not be
shown. This representation gives complete structural formula of any molecule.
H H
H H
H–C–C–H C=C H–C C–H
H H H H
3. Condensed structure –In condensed structural representa tion, dash structures can further
abbreviated by omitting some or all of the dashes representing covalent bonds and by indicating
the number of identical groups atta ched to an atom by a subscript. The resulting expression of
the compound is now called a condensed structural formula. For example, CH3 CH3 , CH2 =CH2,
CH  CH, CH3 OH. Similarly, CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH3 can be further condensed to
CH3(CH2 )6CH3.
4.
 
Bond line structure – In this representation of organic molecules, carbon and hydrogen atoms
bonded to carbon are not shown and the lines representing carbon-carbon bonds are drawn in
zigzag fashion.
Even without writing the hydrogen atoms we know that they are there and we assume that any
carbon atom that does not appea r to have its potential for four bonds sa tisfied is also atta ched to the
appropriate number of hydrogen atoms.
We also rub out all the C representing carbon atoms and write only zig-zag line assuming that every
kink in the line represents ca rbon atom.
Pentane Cyclohexane Benzene

As the functional groups are the key to the organic chemistry so they are specifically shown if present
so the only atoms specifically written are heteroatoms such as oxygen, nitrogen, halogens, which makes
the functiona l groups, which we will discuss later.

This H is shown because

every kink in the these C atoms must also carry it is attached to an atom
chain represents 2 H atoms because only 2 bonds other than C
a C atom are shown for each atom
OH
end C have 3 H these C atoms must also carry O

atoms 1 H atom because only 3 bonds all 4 bonds are shown to
are shown for each atom this c atom so no H
atoms are implied
Organic molecules should be drawn to be realistic, economical and clear so here are 3 guidelines,
which help you make structure more realistic.
 Guideline 1- Draw the chain of atoms as zigzag.
 Guideline 2 – Miss out the hydrogen attach to carbon atoms, along with the C-H bonds.
 Guideline 3 – Miss out the capital C representing carbon atoms.
5. 3D structure – Of course, all the structures we have drawn give only an idea of the real structure
of the molecules. For example, the central carbon a tom of CH3 CH(NH2 )COOH has tetrahedral
arrangement around it but so far we have completely ignored it. Now we want to emphasize
this fact, so for this 3D structure of molecules are written using wedge-dashed projection and
Fischer projection.
COOH
H2 N CH 3
H
A. Wedge-dash projection or perspective formula:-
In this wedge-dash projection, the solid wedge ( ) is used to indicate a bond projecting
above the plane of paper, towards the observer and dashed wedge ( ) is used to depict the
bond projecting below the plane of the paper and away from the observer. The bonds lying in
the plane of the paper are depicted by using a normal line ( ).
 bonds are in H
bonds are away
from the observer
(Dashed wedge)

the plane of paper
(Normal line) C H
H
H
bonds are towards the observer
(Solid wedge)
Sometime we could miss out the hydrogen atom and draw something bit nea ter though slightly less
realistic. Here we assume the missing hydrogen atom is below or above the plane by looking the 3
attachments. If two bonds are in the plane and one is above the plane then hydrogen must be certainly
below the pla ne and similarly if two bonds are in the plane and one is below the plane then hydrogen
must be above the plane.

NH2 NH 2
H or
CH 3 COOH CH 3 COOH
H is assumed to be below the plane
NH2 NH 2
H or
CH 3 COOH CH 3 COOH
H is assumed to be above the plane
B. Fischer projection:–
In this projection molecule is represented by horizontal and vertical lines. Groups on horizontal
line are above the plane (towards the observer) and groups on vertical line are behind the plane
(away from observer) and point of intersection of horizontal and vertical line is carbon.
H
C H
H
H 109.5°
Perspective formula of methane

 

Section
4
Reason for the formation of large number of
organic compounds
What makes the carbon so special?

What is it that sets carbon apart from all other elements in the periodic table?
Why are there so many organic compounds?
The answer lies in carbon’s position in the periodic table. Carbon is in the centre of second row
elements
Li Be B C N O F
Elements of the second row of the periodic table
First think why molecules are formed from atoms? It is because of the reason that atoms combines
with same or with other atoms to form molecule so as to complete its octet and attain lower energy state
and hence become stable. That is the reason why noble gases are considered as inert gases, they generally
do not combine with itself or with other atoms because they have complete octet. But wha t about other
atoms? They have incomplete octet, so they must combines with same or other atoms to form molecule
for better stability.
 
Elements on the left hand side of carbon have less than 4 electrons in the valence shell (Li-1, Be-2, B-
3) so they have more tendencies to loose electron to attain noble gas configuration for stability. That’s
why they generally forms compounds with Li+, Be2+, B3+ by losing 1, 2, 3 electrons respectively. Elements
present downside in the same group too have similar tendency as that of Li, Be and B, hence form
compounds in the following states; Na+, K+, Rb+, Cs+, Mg2+, Ca 2+, Sr2+, Ba 2+, Al3+, Ga 3+,etc.
Elements on the right hand side of carbon have more than 4 electrons in the valence shell (N-5, O-6,
F-7). To complete their octet, valence electrons must be subtracted from 8 that’s why the valency of N is
(8-5) i.e. 3, O is (8-6) i.e. 2 and that of F is (8-7) i.e. 1. It is much easier to gain 3, 2, 1 electrons to complete
their octet as compared to loosing 5,6,7 electrons to complete their octet. So these elements have more
tendency to gain electrons and form compounds in the following states; N3-, P3-, As3-, Sb3-, Bi3-, O2-, S2-, Se2-
, Te2-, Po2-, F-, Cl-, Br-, I- .
As elements present on the left hand side of carbon loose electrons to form compounds and elements
of right hand side gain electrons to form compounds so compounds formed are ionic in nature.
But think about carbon and the elements present down side, which are present in the middle of each
period and have equal tendency to loose or gain electrons as they have 4 electrons in their octet. This led
carbon and other elements of this group (Si, Ge, Sn & Pb) to share electrons with itself and other elements
of periodic table to complete octet. As these compounds are formed by sharing of electrons so they are
considered to be covalently bonded.
Carbon by sharing its electrons with other carbon atoms lea ds to formation of long chain carbon
compounds which may be single, double or triple bonded, cyclic or acyclic, linear or branched. This self-
linking property of carbon is called catenation. All the atoms of 14 th group show the property of catenation
but it decreases down the group beca use of weak overlapping due to large size and follows order:
C > Si >> G e > Sn > Pb
Carbon may also form multiple bonds with N, P, O, S etc. forming large number of functional group,
which we will discuss later.
This is not the end of compound formation. Carbon forms many abnormal compounds with elements
of s, p & d blocks. So for sake of simplicity we are constructing an organic chemist’s periodic table with
the most important elements emphasized.
Elements, which are in dark box, are generally involved in making organic compounds along with
deuterium (D), which is an isotope of hydrogen (H).
Carbon
1 18
At. mass = 12.01 At. radius = 67 pm
H 2 Valency = 4 E. Con. = [He]2s2p2 13 14 15 16 17 He
Li Be EN = 2.5 Structure = Hexagonal B C N O F Ne
Na Mg 3 4 5 6 7 8 9 10 11 12 Al Si P S Cl Ar
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
Cs Ba Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg
La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu D
Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr T
As there are large number of atoms in periodic table which have valence electrons, atomic orbital of
carbon may overlap with them and share its electron to form la rge number of compounds. But for that
many other factors such as size, activation energy, electronegativity, electron affinity, catenation etc. are
 
responsible which all come under one word “Position” i.e. position of carbon in the periodic table. This
word “position” include everything related with molecule formation therefore the main reason behind
large number of organic compound is the position of carbon in the periodic table.


Section
5 Functional Groups
A functional group is an atom such as halogen (-X) or group of atoms such as carboxylic acid
(-COOH) in a molecule that gives the molecule its characteristic chemical properties. They are the action
group or reactive site in a chemical reaction and the remaining hydrocarbon part remains inert.Each
functional group undergoes characteristic chemical reaction so by recognizing them it is possible to
predict the reaction, which that molecule undergoes.
HO CH 3
CH3 Inert
Carboxylic acid hydrocarbon part
The concept of functional group is important for orga nic chemistry due to 3 reasons:
 Each functional group shows its characteristic chemical reaction i.e. a particular functional group
shows same nature of chemical reaction when present in any compound.
 Functional group helps in nomencla ture of organic compounds. Each functional group have a
secondary suffix for it such as oic acid for carboxylic acid, ol for alcohol, etc.

 
Functional group serves to classify organic compounds into different classes or families i.e.
Compounds with same functional group belong to same class.
A molecule may have more than one functional group and are called as poly functional group
compounds or simply poly functional compounds and properties of each functional group may be
modified by the presence of other.
O O
HO Ketone
OH
Carboxylic acid Alcohol
(Polyfunctional compound)
As carbon ha s 4 valencies therefore compounds with all single bond, one double bond or with one
triple bond may be formed with any atoms, which satisfy octet rule.
 Functional group with  bond only-
Carbon may combine with those atoms which needs 1 electron for completing their octet (such
as hydrogen or halogen) or with some groups which require one electron for completing octet
such as alkyl group (–CH3 , –CH2 CH3 , etc.), hydroxyl group (–OH), alkoxy group (–OCH3 ,
–OCH2 CH3 ), amino group ( –NH2 ), thiol group ( –SH) or thioether (–SCH3 ) to form corresponding
functional groups.
| | | |
– C – H/C – Alkane – C – X Alkyl halide – C – OH Alcohol
| | | |
|
– C – SH Thiol C – O – C Ether C – S – C Thioether
|
C – N– H 1 amine C – N– C 2 amine C – N– C 3 amine

| | |
H H C
 Functional group with one  bond-
Carbon forms 1  bond with many atoms such as O, N, S, P and even itself leading to formation
of different functional groups.
 Along C=O bond
O O
 
H/C – C – H Aldehyde H/C – C– X Acid halide
O
Carboxylic O O Acid
  
H/C– C –OH acid H/C– C –O– C –H/C anhydride
O O
 
H/C – C – N– H 1 amide H/C – C– N– C 2 amide
| |
H H
O

O
H/C – C– N– C 3 amide 
|
C – C – C Ketone
C
 Along C=N bond
C/H
C=N–H Imine
 C/H
C=N–R
Alkyl imine

(Schiff base)
C/H C/H
R/H R/H
C=N–OH Oxime C=N–NH 2 Hydrazone
R/H R/H
C/H
C/H
C=N–N NO 2 2,4-Dinitrophenyl
C=N–N–Ph Phenylhydrazone C/H
C/H H NO hydrazone
H 2
C/H O
C=N–N–C–NH 2 Semicarbazone
C/H
H
 Along C=C, C=S and C=P bond
Ph
S=C=S Carbon disulphide C=C Alkene H2C=P Ph Methylene triphenylphosphene
Ph
 Functional group with two  bond-
H/C C/H Alkynes C/H C N Nitrile (Cyanide)
H/C N C Isonitriles (Isocyanide)
 Carbon do not form 3  bonds with any atom
As the size of carbon is so small it do not form compounds which have 3  bonds. This does not
mean that no compound with 3– bonds exists. There are some d block elements, which form 3  bonds
and total four bonds. In that case there are 1  , 2  & 1  bonds. This  bond indicates the 3rd  bond.
Stable quadruple bonds are most common among the transition metals such as rhenium, tungsten,
molybdenum & chromium. Some common examples are
Chromium (II) acetateCr2 (  -O2 CMe) 4 (H2 O)2 ,
Potassium octachlorodirhenate (III), K2 [Re2 Cl8 ].2H2 O &
Potassium octachlorodimolybdate K4 [Mo2 Cl8]
2-
Cl Cl
Cl Cl
Re Re
Cl
Cl Cl Cl
Along with these functional groups there are some other functional groups which are also
encountered in organic chemistry. So learn these too with very carefully so that your understanding
about functional group should be crystal clear. We have used R for alkyl group, which means simply the
hydrocarbon part of the molecule. It may be acyclic or cyclic but attachments are same as given above or
below. For more simplicity trea t R as C so that you should get a better observation in molecules. These
additional functional groups are
O R R
O
R R O O O O
 
–
O O R O H R
Benzene Carbonate ester Carboxylate Hydroperoxy Peroxy
O O
S R–O O–R HO O–R
HO O–R
R R N R
H H R H R H R R
Carbonothionyl Imide Hemiacetal Acetal Hemiketal
R–O O–R R–O O–R R–O O–R H R

R–N R–N
R R R O–R R–O O–R H H
Ketal Orthoester Orthocarbonate ester 1° Amine 2° Amine
R R R
R–N R–N + – N=N R O N
R HN=N =N
R R R Cyanate
3° Amine Azide
4° Ammonium salt Azo

– –
O R N + O
R–N=C=O O–N+ R N C
+ –
O R–N
O
Isocyanate R O O
Isonitrile Nitroso oxy
Nitrate Nitro
O O O
N R–S–OH R S S R–S–R
R O S R
O R R O
Nitroso Disulfide
Sulphonic acid Sulfinile Sulfonyl
O
R S N
R–S–OH
Thiocyanate
Sulfino
While identifying a functional group, look at its attachments very carefully. Same group with different
attachements may become different functional group. You will be surprised to note tha t same group
such as –OH when attached to single bonded carbon is alcohol, with benzene ring it is phenol, with C=N
it is oxime and with C=O it is called as carboxylic acid.
H3 C OH OH O
H3 C
N OH H 3C
H3 C CH 3 OH
H3 C
Alcohol Phenol Oxime Carboxylic acid
Similarly many other differences are observed just on the basis of attachment such as
H3 C Cl Cl O
Cl
H2 C H2 C
H3 C CH 3 Cl H3 C Cl
Vinyl halide Allyl halide
Alkyl halide Aryl halide Acid halide
O O O
H3 C O CH 3 H3 C O CH 3 H3 C O CH 3
Ether Acid anhydride
Ester
R NH 2
 O N
NH 2

R NH 2 R R
Amine Amide Hydrazone
As whole orga nic chemistry is based on functional groups and their interconversion so revise these
functional groups regularly for best picture of organic chemistry in mind.


Section
6
Homologue & Homologous series
A series of compounds in which members have same functional group but differ by one or more
–CH2 – units (molecular weight 14 or multiple of 14) is called Homologous series (homos is Greek word
which means the same as). Members of homologous series are called homologues. Homologues are the
compounds with same general formula and possess similar chemical properties due to presence of same
functional group (if any) i.e. all carboxylic acids a re homologues to each other starting from formic acid
(HCOOH) to any carboxylic acid with formula RCOOH where R is any acyclic saturated alkyl group. All
alkanes starting from one carbon to infinite carbon are homologues.
Example: 1
(A) CH 4 
(B) CH 3 – CH3  Homologous sereis

(C) CH 3 – CH2 – CH 3  of alkanes

(D) CH 3 – CH2 – CH 2 – CH3 
Example: 2
O O O O
(A) CH –C–OH (B) CH –CH –C–OH (C) CH –CH –CH –C–OH (D) CH –CH –C–O–CH
 
3 3 2 3 2 2 3 2 3
Here (a), (b), (c) are homologues but (d) is not homologue of (a), (b), (c) as it has different functional
group.
 One point should always kept in mind that homologues have same functional groups or in
other word have same type of chemical reactions so never insert CH 2 unit to any bond which
create a compound with different functional group.
O O
H H
H O H 3C O
Insert CH 2 unit Homologues
O O
H H H 3C H
CH2 O O
Insert CH2 unit Homologues

Insert CH 2 unit
O O
H CH 3
H 3C O H 3C O
Carboxylic acid Ester
Not Homologues
 As the compounds within a homologous series have the same general molecular formula
and the same functional group (amines, alcohol, carboxyl acid, ester, alkane, alkene, alkyne
etc.), so they can be prepared using similar methods. Such as
OH O
Cu/Heat
R CH 3 R CH 3
We can prepare any methyl ketone from any alcohol having CH3 CH(OH)– (by changing the
number of carbon in R) as Cu/heat is used to convert secondary alcohol into ketone, which we
will study later. Similarly we can prepare any carboxylic acid from primary alcohol (by changing
the number of carbon in R) using KMnO 4 /heat
O
KMnO 4 /Heat
R OH R OH
Compounds within a homologous series show gradual change in physical properties due to
increased molecular size and mass, caused by the longer carbon chains. For example, ethane
(CH3 CH3 ), has a higher boiling point than methane (CH4 ). It is because of the reason that ethane
molecule experiences intermolecular attraction force than methane, as in a large molecule, the
electron cloud tends to be distorted at random to a greater extent. Thus, the London Dispersion
Forces between ethane molecules are higher than that between methane molecules, resulting in
stronger forces of intermolecular attraction, raising the boiling point.
By observing the relative number of carbon and hydrogen atoms in acyclic alkanes it has
general formula CnH2n+2 where n is any integer. So if alkane has 1 carbon atom it must have 4
hydrogen atoms; if it has 2 carbon atoms then it must have 6 hydrogen atoms and so on. As we
 
k now that carbon form s fou r cov al ent bond s and hy d rogen form s onl y one so there i s onl y one
possible structure for an alkane with molecular formula CH4 (methane) and only one structure
for an alkane with formula C2 H6 (ethane). As the number of carbon increases the number of
possible structures also increases. For example C4 H10 have two, C5 H12 have three, C6 H14 have 5,
and C7 H16 have 9 possible structures. This number increases very rapidly as the number of carbon
increases such as C10 H22 have 75 and C15 H32 have 4347 possible structures which we will call later
as constitutional isomers.
As C15 H32 have 4347 possible structures but all are having same molecular formula so they are
simply constitutional isomers which we will study later but starting from CH4 , C2 H6 , C3 H8 to
C15 H32 they differ (CH2 )n unit, so they all are considered as homologues and have same nature of
chemical reactions and method of preparation. We use only the letter R for general alkyl group
(alkane –1H) starting from 1 to infinite.

Here is a table, which helps you to understand homologue better with general formula
Homologous series General formula (Functional group if any) Example
Alkane CnH2n+2 (n=1) CH4 , n=1
Alkene CnH2n (n=2) C2 H4 , n=2
Alkyne CnH2n-2 (n=2) C2 H2, n=2
Alcohol CnH2n+1 OH (n=1) CH3 OH, n=1
Carboxylic acid CnH2n+1 COOH (n=0) CH2 O2, n=0
Carbohydrate Cn(H2 O)y (n=3) C6 H12 O6 n=6
There are some direct chemical reactions from which we can convert one member of a homologous
series to the next member and such reactions are called as homologation reactions that we will study in
chemical reactions
O O O
SOCl 2 CH 2 N 2 R
R OH R Cl moist Ag 2O OH
Carboxylic acid Next higher homologue of
carboxylic acid

 

Section
7
Nature of C, H & Functional groups
When you carefully look over the organic compounds then you will find that carbon atoms are bonded
with other carbon atom or some other atoms such as H, N, S, P, O, X etc. to form molecule. This difference
in attachment leads to difference in rate of chemical reactions. So it is important to analyze carefully the
atoms directly attached to carbon in a ny organic molecule. On the basis of attachment of carbon with
other carbon atoms, the carbon atoms in orga nic compounds are classified into four types
 Primary carbon (1 0 C) – Carbon atta ched to none or one carbon is called as primary carbon. In
case when no other carbon is attached then such carbon is sometime called as super primary
carbon such as CH4.
 Secondary carbon (2 0 C) –Carbon attached to two carbons is called as secondary carbon.
 Tertiary carbon (3 0 C) – Carbon attached to three carbon is called as tertiary carbon.
 Quaternary carbon (4 0 C) – Carbon attached to four carbon is called as quaternary carbon.
These carbon atoms may be in open chain or in ring; they may be neutral, charged or in radical form.
But the important part is the attachment with other atoms and for simplicity they are generally written
with single bonded forms. These forms may be derived from alkane, alkyl halide, alcohol, ether, amines,
thioethers, thiols, etc.
 H3 C
1°
3°
2°
1°
CH 3
2°
2°
1°
CH 3
3°
4°
2°
2°
1°
H3 C 4°
1°
CH 3
3°
3°
1°
CH3
2° 1°

1° CH H3 C
3
H3 C CH 3 1° CH 3 CH 3
1° 1° 1°
 Hydrogen’s a ttached at primary, secondary, tertiary carbons are called primary, secondary &
tertiary hydrogen respectively. It is important to note that carbons are of four types but
hydrogen’s are only of three types, as quaternary carbon does not have any hydrogen.
 Only in case of methane primary carbon have 4 H but in all other alkanes and cycloalkanes each
1 0 , 2 0 , 3 0 carbon have 3, 2, 1 H respectively. To find out total number of 10 , 2 0 , 3 0 ,4 0 carbon and 1 0,
2 0 , 3 0 hydrogen’s you have to count all the carbons or hydrogen of similar types.
 In organic compounds other than alkane or cycloalkanes you must be more careful in reporting
the number H as individual carbon may have any number of H ranging from 3 to 0 as these
hydrogen are already replaced w ith some other atoms or groups.

1°
1°
CH3 1° Cl 2° 1° H
H3 C N 2° 2° CH 3 1°
H3 C N
O 3°
2°
Cl 2°
NH
1° 1°
CH3 O
1°
H3 C 2° S Br
2°
2°
HS 2° NO 2
CH 3 1°
1°H=15
1° 1°H=5 1°H=4
2°H=2 2°H=8 2°H=2
3°H=0 3°H=0 3°H=0
 In organic chemistry some functional groups are formed just by replacement of one hydrogen,
with an atom or groups such as alkyl halide, alcohol, primary amine, thiol, nitro compounds,
sulphonic acid, etc.
OH NH 2
–H –H
H3 C–CH 3 H 3C H3 C–CH 3 H 3C
+OH +NH 2
Alkane Alcohol Alkane Primary amine
SH NO 2
–H –H
H3 C–CH 3 +SH
H3 C H3 C–CH 3 +NO 2
H 3C
Alkane Thioalcohol Alkane Nitro alkane
SO 3 H
–H
H3 C–CH 3 +SO 3H
H 3C
Alkane Alkane sulphonic acid
So alkyl halide formed from replacement of primary H, secondary H and tertiary H a re called as
primary alkyl halide, secondary alkyl halide and tertiary alkyl halide respectively.
Cl CH3
CH 3 Cl
H3 C Cl
H3 C H3 C CH 3
1° Alkyl halide
2° Alkyl halide 3° Alkyl halide
 
Similarly alcohol formed from replacement of primary H, secondary H and tertiary H is called as
primary alcohol, secondary alcohol and tertiary alcohol respectively.
OH CH 3 CH 3
CH 3
CH 3 OH OH
H3 C OH H3 C OH
H3 C CH 3 OH
1° Alcohol 2° Alcohol 1° Alcohol
3° Alcohol 2° Alcohol 3° Alcohol
But some functional groups are formed by chemical reactions of two same or different functional
groups such as ether, secondary amine, tertiary amine, thioether, ester, amide, acid anhydride, etc.
H 3C CH 3 H 3C CH 3
Alcohol O H+H O –H 2 O O
Alcohol Ether

O O
O O
H 3C CH3
O H+H O –H 2 O
H3 C O CH 3
Acid anhydride
Carboxylic acid Carboxylic acid
O
O
H3 C CH 3
O H+H O –H 2 O
H3 C O CH 3
Ester
Carboxylic acid Alcohol
O
CH3 O
H 3C
O H+H NH –H 2 O
H3 C NH CH 3
Primary amine Primary amide
Carboxylic acid
H 3C CH 3 H 3C CH 3
NH 2 + H NH –NH 3
NH
Primary amine Primary amine Secondary amine
H3 C CH 3 H 3C CH 3
NH 2 + H N –NH 3
N
Primary amine CH 3
H 3C
Secondary amine
Tertiary amine
 So be careful in reporting your answer for amines or amides. Secondary alcohol is that in which
–OH is attached to secondary carbon but secondary amine is that in which nitrogen is directly
attached to two carbon and one hydrogen. Tertiary amine is one in which N is directly bonded
to three carbon. So secondary or tertiary amine may be present over primary, secondary or
tertiary carbon.
H3 C
1° Amine
NH 2
H3 C
NH 2
CH 3
H3 C

CH 3
NH 2
CH 3
1° Amine 1° Amine
H CH 3
NH
N N NH
2° Amine 2° Amine
2° Amine 3° Amine
NH N N N
2° Amine 3° Amine 3° Amine 3° Amine


Section
8
Saturated & unsaturated molecules with
important positions
In organic chemistry when we look over the molecules we will find that some molecules are only
single bonded but some molecules are multiple bonded and tha t multiple bond may be of many types
such as double bonds of C=C, C=N, C=O, C=S or triple bonds of C  N or C  C. To differentiate these
compounds word saturated and unsaturated is used.
To understa nd these terms, take a glass full of water and add a spoon of sugar in it and stir it with
spoon. You will find that whole sugar dissolves in it. But when you continuously go on adding spoons of
sugar in it and stirring it then after some time you will find that dissolution stop and sugar settles at the
bottom of it. At that time you will say that no more sugar is dissolving in it i.e. it is saturated. Similarly
when no further bond can be added to a molecule at room temperature then such compounds are called
as saturated compounds and if further bonds can be added in it then they are called as unsaturated
compounds. As we know that single bond has no tendency to add anything at room temperature and
have only tendency to substitute some atom or group so they a re considered as saturated compounds
and multiple bonded compounds have tendency to add bond so they a re considered as unsaturated
compounds.
A – B  C 
A – C  B A  B  C – D 
 A– B
Substitution reaction Addition reaction | |
C D
 
Saturated compounds may be cyclic or acyclic; may be only of carbon and hydrogen or may have
some hetero atoms such as halogens, nitrogen, oxygen or sulphur. The multiple bond may be of any
form such as C=C, C=N, C=O, C=S, C  N or C  C with or without rings.
Example of saturated compounds are-
Cl OH NH 2
H3 C CH 3 H3 C H3 C H3 C CH 3
CH 3 CH 3
SH
O S
H3 C CH 3 H3 C CH 3 H3 C CH 3
OH
NH O
N
H S

Example of unsaturated compounds are-
O O
H3 C CH 2 H3 C CH H3 C
H3 C H CH 3
O O O
H3 C OH H3 C NH 2 H3 C OMe
OH
NH O
N S
If compounds are saturated with presence of only carbon & hydrogen then such compounds are
called as saturated hydrocarbon, such as alkane and cycloalkane but if any hydrogen in it is replaced
with any other atom or group such as –Cl, –OH, –NH2 , –SH then they are considered as derivatives of
saturated hydrocarbons. Similarly if compounds are unsatura ted and have only carbon & hydrogen,
they are called as unsaturated hydrocarbon such as a lkene, alkyne, cycloalkenes & cycloalkynes but if
hydrogen in it is replaced with any atom or group then they are considered as derivatives of unsaturated
hydrocarbon.
CH3 CH 2 CH 3  CH 3 CH 2CH2 Cl

Alkane Derivative of alkane
CH2 =CHCH3  Cl–CH=CHCH3

Alkene Derivative of alkene
When you aga in carefully analyze the functional groups you w ill find that some functional groups
have presence of carbon within it such as nitrile (–CN), aldehyde (-CHO), ketone (-CO-), carboxylic acid
(-COOH), acid halide (-COX), acid anhydride (-COOCO-), ester (-COOC), amide (-CONH2 ) etc but some
functional groups do not have carbons such as a mine (–NH2 ), alcohol (-OH), thiol (-SH), nitro (-NO2 ),
Sulphonic acid (-SO3 H), ether (-O-), thioether (-S-), etc.
In organic chemistry some common positions such as zero (0), alpha ( ) , beta () , gamma ( ) , delta
() , and epsilon ( ) have been commonly encountered so we must have a clear cut picture of it too.
 
If any functional group do not have carbon in it then the carbon directly attach to it is given the
position alpha followed by beta, ga mma, delta and epsilon to next carbons in sequence such as
δ β δ β β
ε Cl ε OH ε δ NH 2
H3 C α H3 C α H3 C α
β β
β β β H3 C α CH 3
β CH 3 H3 C α CH 3 δ
H3 C α
δ δ
O CH 3
NO 2 SO 3 H
α β
α
CH 3 β
α α β β β
+
α S+ α β
+
H3 C N CH 3 α N α
CH 3
α H3 C α
CH 3 α CH 3 CH 3
β α

But if any functional groups have ca rbon in it then that carbon is give position zero followed by
alpha, beta, gamma, delta and epsilon to next carbons in sequence such as
O β O O
β β
ε δ ε δ ε δ
H3 C α 0 H H3 C α 0 OH H3 C α 0 Cl
β δ β δ δ β
H3 C α
β CH 3 H3 C α
β CH 3 β δ εO
α
α 0 0
CH 3 β α O
0 COOCH 3 0 COOCOCH3 O β
This zero (0), alpha ( ) , beta () , gamma ( ) , delta () , and epsilon ( ) have very much importance
in organic chemistry as many named reactions such as Aldol reaction, Cannizzaro reaction, Claisen
rearrangement, HVZ reaction etc involve these terms, which we will study later.
 Aldol condensation- When aldehyde having alpha hydrogen is treated with base, it first give
beta hydroxy aldehyde which later looses a water molecule to form alpha,beta-unsaturated
aldehyde as a product.
O OH O O
Base Δ
CH 3 –C–H CH3 –CH–CH2 –C–H CH 3 –CH=CH–C–H
α 0 β α 0 β α 0
Aldehyde β-Hydroxy α ,β-unsaturated
having α –H aldehyde aldehyde

 

Section
9 Hybridization
When we carefully look over the organic molecules we will find that some carbon atom is single
bonded while some others are multiple bonded. These single or multiple bonds create some fixed shape
or geometry in molecule such as linear, planner, tetrahedral, etc. Molecular geometry or molecular
structure is the 3-dimensional arrangement of the atoms that constitute a molecule. It determines several
properties of a substance including its reactivity, polarity, phase of matter, color, magnetic properties,
and even biological activities. The molecular geometry can be determined by various spectroscopic
methods & diffraction methods such as Infrare d (IR), microwave & Raman spectroscopy can give
information about the molecule geometry. X-ray crystallography, Neutron diffraction and Electron
diffraction can give molecular structure for crystalline solids based on the distance between nuclei and
concentra tion of electron density. Gas electron diffraction can be used for small molecules in the gas
phase. Nuclear magnetic resonance (NMR) & Förster (Fluorescence) resonance energy transfer (FRET)
methods can be used to determine complementary information including relative distances, dihedral
angles, angles, and connectivity. Molecular geometries are best determined at low temperature and can
be different as a solid, in solution, and as a gas.
As you learned earlier that these single or multiple bonds are formed by overlapping of atomic
orbitals either by axial overla pping or by lateral overlapping, molecular geometries can be specified in
 
terms of bond lengths, bond angles and torsional angles.The bond length is defined to be the average
distance betw een the centers of two atoms bonded together in a ny given molecule. A bond angle is the
angle formed between three atoms across at least two bonds. For four atoms bonded together in a chain,
the torsional angle is the angle between the plane formed by the first three atoms and the plane formed
by the last three atoms.
To explain the shape of any molecule new concept of hybridization was proposed which is mixing of
atomic orbitals of same or nearly same energy and redistribution of energy to form new hybrid orbitals
of equal energy a nd same shape. So hybridiz ation is simply a mathematical approach to explain the
shape of any molecule i.e. if a molecule is tetrahedral then its tetrahedral shape is explained by sp3
hybridization and similarly if a molecule is planner then to explain it w e have to use the concept of sp2
hybridization and for linear molecules sp hybridization. In organic chemistry when we have to find out
hybridization of any atom always count the number of sigma bond and lone pair of electrons present on
it (if any).

120° 180°
109.5°
A A A
Tetrahedral shape Planner shape Linear shape
As the shape of atomic orbitals is derived from Schrodinger wave equation so it is purely a
mathematical term. Some shapes commonly encounted in chemistry are
A. Linear shape B. Trigonal planner

C. Bent shape D. Tetrahedral shape
E. Trigonal pyramidal F. Trigonal bipyramidal
G. Seesaw H. T shaped
I. Octahedral J. Square pyramidal
K. Square planar L. Pentagonal bipyramidal
M. Pentagonal pyramidal N. Planner pentagonal
O. Square antiprismatic P. Tricapped trigonal prismatic
As organic compounds are carbon containing compounds and carbon has only s and p orbitals so the
hybridization commonly observed in organic chemistry are sp, sp² & sp³. To calculate hybridization of
any atom alw ays counts the number of sigma bonds and lone pair of electrons present on it.
 If the sum of number of sigma bonds and lone pair of electrons = 2, atom have sp hybridization.
 If the sum of number of sigma bonds and lone pair of electrons = 3, atom have sp² hybridization.
 If the sum of number of sigma bond and lone pair of electrons = 4, atom have sp³ hybridization.
There is no role of positive charge in calculating the hybridization of any atom as tha t contains no
electrons or bonds. Negative charge is also considered as 2 electrons system similar to lone pair.
H sp 2 sp
 
sp 3 sp2 sp 2
sp3 sp
2
CH 2 sp2 CH
H H
H3 C – OH H2 C 2 H2 C sp
H sp
sp3 sp3 sp2

2
O 2 sp2 sp
sp2 sp sp2 3 sp2 sp
sp
H2 C C CH 2 sp3 sp2 sp2
sp 3 CH 3 sp2 sp2 sp 2
As we told you earlier that it is simply a mathematical approach to explain the shape of molecule so
there may be some violation of it. These violations are commonly of three types:
 If system ha ve A=B-C, where C have lone pair of electrons then one of the lone pairs present is
not counted for hybridization and geometry along C is planner & its hybridization will be either
sp or sp²
H2 C . sp
.O–H 2
H2 C .. sp 2 H2 C . sp
.S–H 2
.. NH 2 ..
 If system have A=B-C, where C ha ve negative charge then –ve charge is not counted for
hybridization and geometry along C is planner & its hybridization will be either sp or sp²
sp 2 H2 C sp 2
H2 C sp 2
CH –
2
H2 C
.O–. ..NH –
 You must remember these two structures where all atoms are sp² but molecule is not planner at
all.
or (Non Planner)
Cyclooctatetraene = COT Overall Tub shaped
or H H (Non Planner)
10 Annulene Hydrogens present in the central
carbon disturbe the plane

 

Section
10 Classification of organic compounds
Up to this point you are familiar w ith the common functiona l groups, saturated and unsaturated
compounds with their hybridization and shape so now we can classify the organic compounds into
different categories on the basis of their shape and stability. Organic compounds are divided into two
classes- Acyclic or aliphatic & cyclic compound. Acyclic compounds or aliphatic compounds are those
which do not have any ring. The word aliphatic comes from aleiphar which mean fat or oil. Here carbon
atoms can be joined together in straight chains or branched chains. They can be saturated, joined by
single bonds (alkanes), or unsa turated, with double bonds (alkenes) or triple bonds (alkynes). Besides
hydrogen, other elements can be bound to the carbon chain, the most common being oxygen, nitrogen,
sulfur and halogen. The simplest a liphatic compound is methane (CH4 ). If aliphatic compounds are
cyclic in nature then such compounds are called as alicyclic (Aliphatic + cyclic) such as cycloalkanes,
cycloalkenes, cycloalkynes, cyclic esters, cyclic ketones etc.
 Aromatic compounds are the most important class of organic molecules due to their extra stability.
Many natural products such as DNA, RNA, hemoglobin, chlorophyll, medicines, and polymers
are aromatic in nature. For a compound to show aromatic nature it must follow these four
conditions.
(I) Compounds should have at least one ring.
(II) Each atom of the ring should have sp² or sp hybridization, no matter it is made up of C, N, S, O

or any other atom.

(III) The ring should be planner or nearly planner, so that effective overlapping of pi bond is possible.
(IV) The ring should follow Huckel’s rule i.e. the ring must ha ve (4n + 2)  electrons, w here n is any
number starting from 0 to  . If the value of n=0, ring must have 2  electrons; for n=1, 6 
electrons must be present a nd so on.
If any compound violates any of the above conditions then it will not be considered as aromatic and
not get extra stability. For example, Hexa-1,3,5-triene (CH2 =CH–CH=CH–CH=CH2 ) follows last three
conditions but violates the first one so is not an aromatic compounds.
 Aromatic compounds are further of two types – one with attachment of benzene nucleus and
other with absence of benzene nucleus. Those which contain benzene ring are called benzenoid
while those which do not have benzene ring are considered as non-benzenoid.
 Cyclic system may be homocyclic (carbocyclic) where each atom of the ring is made up of carbon
or may be heterocyclic where at least one atom of the ring is hetero atom such a s N, S or O.

Examples of 2 pi electrons aromatic system:
–
HO O Ph Ph O O
+ O
+
+ + –
HO O Ph Ph O O
NC CN – –
NC CN O O O
+
– +
–
H3 C CH 3 Ph Ph O O
CH 3 –
H 3C N
+ Fe –
N
Dimethyl fulvene Calicene

Ferrocene
Group
+ +
CH 2 +
CH 2
Tropylium ion + Substituted

Benzene
Examples of heterocyclic 6 pi electron aromatic system:
H H CH 3
N O S N N N N
+
N O N
Thiphene N
Pyrole Furan Imidazole Pyridine Pyrylium ion Pyrimidine
Nicotine
NH 2 NH 2 O OH O OH
 
CH 3 CH 3
COOH N N HN N HN N
O N HO N O N HO N O N HO N
N H H
Niacin H
Cytosine Uracil Thymine
NH O S
N N
Naphthalene Quinoline Iso quinolene Indole Benzofuran Benzothiophene
H N NH N NH
N NH N N N N
N N +
Indenyl anion Purine Azulene NH 2 NH
Indole Adenine

H2 N N NH H 2N N NH
N N N
OH O
Guanine
Examples of 14 pi electron aromatic system:
–
+
Anthracene Phenanthrene Phenalenyl anion (14) Annulene
 Anti- Aroma tic compounds are very unstable compounds a t room temperature so they either
dimerize or trimerise to become alicyclic one.
Theoretically Antiaromatic compounds follow these 4 conditions:
 Compounds should have at least one ring.
 All atoms of ring should have sp² or sp hybridization, no matter it is made up of C, N, S, O or any
other atom.
 The ring should be planner or nearly planner, but it is important to note that there no effective
overlapping of pi bond is observed.
 Compound will not follow Huckel’s rule and ring must have (4n)  electrons, w here n = 1 to
H
Some common examples of anti aromatic compounds are:
– +
Cycloprop-2-enide ion Cyclobuta-1, 3-diene Cyclopenta-2,4-dienylium ion

 

Section
11 Baeyer’s strain theory
When we carefully look over the cyclic saturated compounds we find that each atom is sp3 hybridized
so it must have bond angle 1090 28´ but in cycloalkanes this angle is mathematically 180-(360/n) where n
is the number of atoms making ring i.e. in Cyclopropane this angle is 600 ; in Cyclobutane it is 900 and so
on. This difference in desired bond angle and real bond angle causes strain in bond which affects the
reactivity as well as stability of molecule. Greater is the deviation from the theoretical angle greater is the
strain. To calculate the distortion or strain in ring we assume the atoms of ring in a plane, such as in
cyclopropane, all the 3 carbon atoms occupy one corner of an equilateral triangle with bond angle 600 . As
two corners bent themselves to form bond so strain too is divided equally. So strain in cyclopropane will
be ½ (109 028´ – 60 0 ) = +24 0 44´.
109°28'
24°44' 24°44'
60°
Deviation of bond angle in cyclopropane from normal tetrahedral angle
Distortion or strain = ½ (109 0 28´ – bond angle of ring). So angle strains in some cycloalkanes are
listed in the table below.
Compound No. of C in the ring Angle between the C atoms Distortion or strain
Cyclopropane
Cyclobutane
 3
4
60°
90°
 24°44'
9°44'
Cyclopentane 5 108° 0°44'
Cyclohexane 6 120° –5°16'
Cycloheptane 7 128°34' –9°33'
Cyclooctane 8 135° –12°62'
From the table it is clear that cyclopropane has the maximum distortion, so it is highly strained
molecule and consequently more reactive than any of the monocyclic alkanes, which is clear from the
reaction that ring can be opened very easily to relieve strain on reaction with Br2 , HBr or H2 /Ni at high
temperature. In contrast, cyclopentane & cyclohexane have least strain so they are found more readily
and are very stable as compared to cyclopropane.
Baeyer strain theory satisfactorily explains the typical reactivity and stability of smaller rings (from
C3 to C5 ) i.e. Stability order follows : Cyclopropane< Cyclobutane < Cyclopentane

But not valid for cyclohexane onwards because the strain again increases with the increase in number
of carbon a tom but actually large rings are more sta ble. So molecular orbital theory is also considered
according to which covalent bond is formed by coaxial overlapping of atomic orbitals. The greater is the
extent of overlap the stronger is the bond formed. In case of sp3 carbon, C-C bond will have maximum
strength if the C-C-C bonds have th e angle 1090 28´. If cyclopropane is an equilateral triangle then the
bond angle of each C-C-C bond would be 600 . Therefore it was proposed by Couson that in cyclopropane
the sp3 hybridized orbitals are not present exactly in one straight line due to mutual repulsion of orbital
of these bonds resulting thereby loss of overlap. This loss of overlap weakens the bond and is responsible
for its instability and strain in molecule. Similarly, in case of cyclobutane, there is also loss of overlap but
the loss is less than in cyclopropane, so cyclobuta ne is more stable than cyclopropane. Overlapping of
orbitals in large ring compound (5 or more carbon atoms) is however much better which accounts for the
greater stability of such compounds.
H H
C
H C C H
H H
It is natural that when a molecule has strain within it, it will affect the stability of molecule. The
stability of molecule can be calculated easily by measuring heat of combustion which will give the measure
of total strain and thermochemical stability which can be calculated mathematically.
Total strain = (No of C atom in the ring × observed heat of combustion/CH 2 ) - observed heat of
combustion/CH 2 for n alkane.
Experimental data of total strain for different cycloalkanes
No. of C in the ring Heat of combustion KJ/CH2 Total strain in KJ
3 697 120
4 685 112
5 664 35
6 659 12
7 662 35
8 - 11 661 - 665 32 - 88
12-onwards 657 - 661 0 - 48
 
From the da ta above it is clear that strain decreases from C3 to C6 i.e. stability increases, but stability
again deteriorates from C7 to C11 ring system but interestingly increases from C12 and attain the same
stability of six membered ring. According to this theory, the carbon atoms in 5 membered and smaller
rings can lie in one plane as explained by Baeyer but Sachse suggested that in six membered and higher
rings the carbon atoms are present in different plane i.e. the ring is puckered. In this way the normal
valency a ngle 109 0 28´ is retained and the ring produced is completely strainless. Thus he proposed that
cyclohexane exist in two puckered forms as boat and chair form in which chair form is more stable.
These forms a re readily interconvertible through half chair and twist boat forms simply by rotation
about the single bonds which we w ill study later in conformation.
Chair Half chair Twist boat Boat

These forms of cyclohexane are to give a real picture of it but on paper we commonly make its
planner form.

Exercise
01 Subjective Approach
You can’t mug-up organic chemistry because there’s too much of it. You can remember trivial things
like name of compounds but that doesn’t help you to understand the principle behind the subject. You
have to understand the principle because the only way to tackle organic chemistry is to learn to work it
out. That is why we are first providing you some questions so that your understanding about the topic
should be increased. These problems will set you on your way but they are not the end of the journey, as
here you are beginning your journey to understand organic chemistry.
The problem would be of little use to you when you could not check your answers. For the maximum
benefit, you need to solve all the problems without looking the answers. Then you should compare your
answers or suggestions with ours before going to next chapter. If any answer is mismatch then darken
those question numbers with red pen and again have a microscopic look over it and its theory and
correct it before proceeding further. Here starts the first set of 60 questions.
01. What is orga nic chemistry? Write at least 4 characters which distinguish organic compounds from
inorganic compounds.
02. What is the reason behind the formation of large number of organic compounds?
03. Which organic compound was first prepared in laboratory?
04. Which atom is the centre of attra ction in whole organic chemistry?

05. What is the position of carbon in the periodic table?
06. What is Octet Rule?
07. What is electronegativity and electron affinity?

08. What is the electronegativity value of C, H, N, O and F in Pa uling scale?
09. What is the valency of C, H, N, O and F?
10. What is the symbol for the representation of all halogens?
11. Write C-F, C-Cl, C-Br and C-I bonds in decreasing order of their bond strength.
12. Draw structures of single bonded hydrocarbons with 6 carbon atoms having linear, branched and
cyclic frameworks.
H O OH
13. What is wrong in given structure?
H NH
Suggest better way to represent the molecules? H3 C H
H H H
N NH 2

14. What is the carbon carbon bond length in ethane, ethene, ethyne & benzene?
15. Which bond is weaker in C-H & C-C bond of alkane?
16. Write the decreasing order of bond strength of carbon- carbon single, double and triple bond?
17. How many electrons are involved in formation of single, double and triple bond?
18. What are isotopes? Comment on the isotopes of ca rbon & hydrogen?
19. Oxygen has atomic number 8 and have 3 isotopes with molecular mass 16, 17 & 18 respectively. How
many protons, electrons and neutrons does each of these isotopes have?
20. What is Aufbau Principle?
21. What is Pauli Exclusion Principle?
22. What is Hund’s Rule?
23. What is the ba sic difference between Principle and Rule?
24. Potassium has atomic number 19 and atomic mass 39, with one unpaired electron in its valence shell.
Which orbital does the unpaired electron occupy?
25. Write electronic configuration of F (Atomic no. 9), Cl (Atomic no. 17), Br (Atomic no. 35) & I (Atomic
no. 53)?
26. What are ionic, covalent, co-ordinate & polar covalent bonds?
27. Which of the following among given compound have most and least polar bond? Na I, LiBr, Cl2 ‚ ,
KCl
28. What is dipole moment?
29. What is formal charge and how it is calculated in molecules such as H3 O+?
30. Write the Lewis structures of formic acid, formaldehyde & methanol?
31. Determine the partial positive charge on oxygen atom in a C=O bond if it has bond length 1.22Å and
bond dipole moment 2.30 D?
32. Predict the relative length of HF, HCl, HBr & HI bonds?
33. Use the symbol   and  – to show the direction of polarity of the bonds shown in given compounds?
CH3 -Cl, CH3 -NH2 , HO-Br, I-Cl, CH3 -OH, CH3 -MgBr & NH2 -OH

34. Name at least 10 organic compounds which make your life easy?

35. What is functional groups and why they are important in organic chemistry?
36. Name the compound in which -OH group is attach to tetrahedral carbon, C=C, aroma tic ring and
C=O group?
37. Convert these condensed form of molecules into bond line structures.
(A) C6 H5 CH(OH).(CH2 )4 COC2 H5 (B) O(CH2 CH2 )2O
(C) (CH3 O) 2 CHCH=CHCH(OMe)2
38. Draw bond line structures for these compounds showing the hydrocarbon framework clearly and
showing all the bonds present in functional groups
(A) AcO(CH2)3 NO2 (B) MeO2 .CH2 .OCOEt
(C) CH2 =CH.CO.NH(CH2 ) 2 CN
39. What are the probable formula s for the following compounds
GeCl?, AlH?, CH?Cl2 , SiF?, CH3 NH?, AlCl?, CF2 Cl?, NI? & PH?.
40. Why can’t organic molecule having formula C2 H7 , C2 H7 N & C3 H5 Br2 exist at room temperature?
41. Fill the non bonding valence electrons if present that are missing from the following bond line
structure.
O O O
O
H3 C CH 3 H3 C N
H3 C CH 3 H3 C Cl H3 C O CH 3
42. Convert the following molecular formulas into bond line structures leaving lone pair electrons as
they are assumed to be present there
(A) C3 H8 (B) CH5 N (C) C2 H6 O (2 possibilities)
(D) C2 H4 O (3 possibilities) (E) C3 H9 N (4 possibilities)
43. Sodium methoxide (NaOCH3 ) contains both covalent and ionic bonds. Indicate the linkage which
gives a clear cut picture of it.
44. What are homologues? Write at least 4 homologues of methane, formaldehyde, acetone and formic
acid each.
45. How are molecules with a single functional group represented? Write a general formula of alkyl
chloride, alkyl alcohol, a nd alkyl carboxylic acid?
46. How do the compounds in homologous series differ in molecular formula, physica l & chemical
properties?
47. Name the w ord used for sulphur analogs of alcohol & ether?
48. Find out the functional groups present in following compounds
SH SH O
O
H 3C CH 3 H 3C CH 3 O
SH CH 3
Compound with worst smell Compound with worst smell Olean sex pheromone of olive fly
(I) (II) (III)
O OH
N CH 3 H 3C O
H 2C Cl O
N CH 3
Corylone
 
Vinyl chloride Compound from cakes
Compound from coffee
(IV) & biscuits ceramel roasted protein
(V)
(VI) (VII)
OH H
O N CH 3
MeO CHO OH NH 2
CH 3
Zeneca's tenormin HO N
For treatment & prevention Vanillin of vanilla Pyridine Phenol. Aniline
of heart deasese (IX) (X) (XI) (XII)
(VIII)
H H CH 3
N +2 Cl – CH 2 H3 C CH 3 H 3 C CH3 R N S
O–O–H
O N CH 3
O COOH
Diazonium salt Styrene Cummene Cummene peroxide Penicilin
(XIII) (XIV) (XV) (XVI) (XVII)
O EtO
CH 3 H N O
N O CH 3 H3 C
N CH 3 N S
N COOH N NH
O N
HO O H 3C O N
Nicotine Paracetamole
Aspirin Pfizer's sildenafil (Viagra) CH 3
(XVIII) (XX)
(XIX) (XXI)
O
I
NH
CH 3OH H2 C
N OH N O
CH 3 H O CH3 HO O
H3 C N O
O H 3C
H H HO CH3
O Cocaine O N
Testosteron (Hormone) Quinine Fialuridine
(XXIII)
(XXII) (XXIV) (Anti viral compound)
(XXV)
OH Cl O
O O
HN NH S NH 2
H3 C CH 3 NH O O
Cl O OH
Chloroxylenol Indigo dye
Furosemide (Sulpha drug)
(XXVI) (XXVII)
(XXVIII)
49. Give the structural formula for a 3 carbon compound containing each of the following functional
groups
(A) C=C (B) C  C (C) Cl (D) OH (E) CHO (F) C=O (G) C  N
50. Draw one possible structure for each of these molecules selecting any group of your choice for the
“wild card” substituents for
R1 Ar2 O
R2
A
 Ar1 Ar3
51. Find the total number of primary, secondary, tertiary and quaternary carbon in given molecule.

H3 C CH 3 H2 N CH3 CH 3
H3 C CH 3 CH 3 OH Cl
H3 C H 3C CH 3
H3 C CH 3 H3 C CH 3 H3 C CH 3
I II III IV CH 3
CH3 CH 3
CH 3 CH 3 O O
CH 3 HN Br N OH N N
OCH3
O CH CH3 H3 C O
V 3
VI VII
VIII

52. Find the total number of primary, secondary and tertiary hydrogen present in given molecule.
H3 C H3 C CH 3 H3 C CH 3 CH 3
CH 3 CH3 Cl
H3 C CH 3 H3 C CH CH3 H3 C Cl
3
OH O CH
I II III IV CH 3 V 3
53. What are alicyclic compounds? Write at list 10 compounds with different chemical nature.
54. Write the structure of smallest cyclic
(A) Alkane (B) Alkene (C) Alkyne
(D) Ether (E) sec-Amine (F) t-Amine
(G) Thioether (H) Ester (I) Acid anhydride
(J) sec-Amide (K) t-Amide (L) Aromatic compound
(M) Anti-aromatic compound.
55. Write the structure of open chain molecule that meet the following descriptions
(A) Contains 2 sp² hybridized ca rbon and 2 sp³ hybridized C.
(B) Contains only 4 carbons, all sp² hybridized.
(C) Contains 2 sp hybridized carbons and 2 sp² hybridized C.
56. What bond angles do you expect for each of the following and what kind of hybridiz ation do you
expect for the central atom in each case?
(A) The C-O-C angle in CH3 -O-CH3
(B) C-N-C angle in CH3 -NH-CH3
(C) The C-N-H a ngle in CH3 -NH-CH3
(D) The O=C-O angle in acetic acid
57. Write the hybridization of each carbon in the given molecule?
H H H 3C H2 N COOH
H3 C
CH 2 C
H H H2 C OH Cl CH 3
 
I II III V VI VII
IV
NH 2 CH
. CH–2 CH+2 H3 C
CH3 CH 3 H
2 CH 3
HN N CH 3 H H
H3 C
O S CH3 H CH 3
VIII IX
X XI XII XIII XIV XV
58. State whether the given molecules are planner or non-planner.
H H H3 C H2 C +
C CH 2 CH 2
H H
I II III IV V VI VII
H2 C– H3 C
. H2 N H O S
H
N
CH 2 CH 2 CH 2 H N
H XIV
VIII IX X XI XII XIII XV
59. Classify the following molecules into saturated and unsaturated compounds?
Cl H3 C H3 C
H3 C CH 3
H3 C
CH 3 CH 3 HO Br
I II IV V
III
H3 C H3 C H3 C H3 C
CH 3 CH 3 CH 3
VI O O O CN
VII VIII IX X
H3 C H Cl
CN N
H3 C COOH
XII XIII XIV XV
XI
60. Classify the following molecules into aromatic, anti aromatic and non aromatic compounds.
.
I II III IV V VI VII VIII IX X XI XII XIII
XIV XV XVI XVII XVIII XIX XX XXI XXII XXIII
H H
O S N N N
XXV XXVI XXVII XXVIII XXIX XXX XXXI XXXII

XXIV
O O –
O O O
N 2Cl O N OH
+
HO OH N O
+
XXXIII Squaric acid Sydnone Ph Tropone Tropolone Pyrylium ion
XXXIV XXXV XXXVI XXXVII XXXVIII XXXIX
 N+
N–
H3 C CH 3 
Pentalene Heptalene
Phenalenyl anior
XLI XLII XLIV XLV XLVI
XL XLIII
Ph Ph L
XLVII XLVIII XLIX


Answers
Subjective Approach
01
01. Organic chemistry is the chemistry of ca rbon a nd its compounds with some exception of CO3 2– ,
CO, CO2 etc whose properties resembles more with inorga nic compounds. In general organic
compounds
(A) Rea ct more slow ly and required higher temperature for reaction.
(B) Undergoes more complex reactions a nd produce side products.
(C) Ha s lower melting and boiling points with low solubility in w ater.
(D) Are cla ssified into families of compounds such as alcohols, ethers, ca rboxylic acid etc which
ha ve different reactive groups so ha ve different chemical reactions.
02. Position of carbon in the periodic table.
03. Urea
04. Carbon
05. 2 nd period & 1 4 th group.
06. In trying to explain why atoms form bonds, Lew is proposed tha t a n a tom is most stable if it has
a filled outermost shell or an outer shell of eight electrons, which is ca lled a s Octet rule.
According to it, an atom will give up, a ccept, or share electrons in order to achieve a filled shell
or an outer shell that contains 8 electrons.
07. Electronegativity is a chemical property tha t describes the tendency of an atom or a functional
group to attract the bond pair electrons towards itself. An atom’s electronegativity is affected by
 
both its atomic number and the dista nce that its valence electrons reside from the charged nucleus.
The higher the a ssocia ted electronegativity number, the more a n element attra cts electrons
towards it. There are ma ny sca les to measure it but Pa uling sca le is most common a mong these.
Electron a ffinity of a n a tom or molecule is the amount of energy released when a n electron is
added to a neutral atom or molecule to form a negative ion.
X  e – 
 X–
This property is measured for a toms and molecules in the ga seous state only, since in the solid or
liquid states their energy levels would be cha nged by contact with other atoms or molecules.
08. 2.5 , 2.1, 3.0, 3.5, 4 .0 respectively
09. 4, 1, 3, 2 & 1 respectively
10. X
11. C-F > C-Cl > C-Br > C-I
12. Linear, branched a nd cyclic framew orks of 6 carbon hydrocarbons a re

CH 3
H3 C CH 3 H3 C
H3 C CH3 CH H3 C
CH3 3 CH 3
CH 3 CH3 H3 C CH 3
CH3
CH 3
CH 3 H3 C
H 3C H3 C CH 3
CH 3 CH 3
H3 C
CH 3
CH3 CH 3 CH 3
H3 C CH 3 CH 3 H3 C
H3 C
CH 3 CH 3 H3 C CH 3
13. Those structures a re not a ccording to geometry a nd ma y crea te confusions so better

representations are
H
OH
N CH 3
N O H3 C
NH 2
14. 1.54Å, 1.34Å, 1.20Å a nd 1.39Å respectively

15. C-H bond is weak
16. Bond strength follows C  C > C=C > C-C
17. 2, 4 & 6 respectively
18. Isotopes are variants of a pa rticular element such a s C or H. All isotopes of a given element share
the same number of protons but differs in its number of neutrons. The term isotope is formed
from the Greek words “isos” means “equal” and “topos” means “place”, hence: “the same place,”
meaning tha t different isotopes of a single element occupy the same position on the periodic
ta ble. The number of protons within the atom’s nucleus uniquely identifies an element, but a
given element ma y in principle have any number of neutrons. The number of nucleons (protons
and neutrons) in the nucleus is the mass number, and each isotope of a given element has a
different mass number. For example, C-1 2, C-13 & C-14 a re three isotopes of the element carbon
 
with mass numbers 1 2, 13 and 14 respectively. The a tomic number of carbon is 6 which mea ns
that every carbon a tom ha s 6 protons, so that the neutron number of these isotopes are 6,7 & 8
respectively.
H ha ve three naturally occurring isotopes, sometimes denoted as 1H (Hydrogen), 2H (Deuterium,
D), a nd 3 H(Tritium, T) with 1 proton a nd 1 , 2 , 3 neutron respectively.
19. Ea ch isotopes of oxygen have 8 protons & 8 electrons but have 8,9,1 0 neutrons respectively.
20. Aufba u principle (German word, Aufba u meaning “ building up, construction” ) is used to
determine the electronic configura tion of a n a tom, molecule or ion. The principle postula tes a
hypothetica l process in w hich a n a tom is “built up” by progressively adding electrons. As they
are added, they assume their most stable conditions (electron orbital) with respect to the nucleus
and those electrons alrea dy there. According to the principle, electrons fill orbita ls sta rting at
the lowest available (possible) energy levels before filling higher levels (e.g. 1s before 2s). The
number of electrons that can occupy each orbital is limited by the Pauli Exclusion Principle&
Hund’s rule.

21. Pa uli Exclusion Principle is the quantum mechanica l principle that sta tes tha t no two identical
fermions (pa rticles with half-integer spin) may occupy the same qua ntum state simultaneously.
A more rigorous sta tement is that the total wave function for two identical fermions is anti
symmetric w ith respect to exchange of the particles. For example, no two electrons in a single
atom can have the same four quantum numbers; if n,l, and ml a re the same, ms must be different
such tha t the electrons have opposite spins, and so on.
22. Hund’s rules refer to a set of rules which are used to determine the term symbol that corresponds
to the ground state of a multi electrons a tom. In chemistry, the first rule is especia lly importa nt
and is often referred to as simply Hund’s rule.
 For a given electronic configuration, the term w ith ma ximum multiplicity has the lowest
energy. The multiplicity is equal to2S + 1 , w here S is the total spin a ngular momentum for
all electrons. The term w ith lowest energy is a lso the term with ma ximum S.
 For a given multiplicity, the term with the largest value of the orbital angular momentum
number L ha s the low est energy.
 For a given term, in an atom w ith outermost sub shell ha lf-filled or less, the level with the
lowest value of the total angular momentum quantum number J (for the opera tor J = L + S)
lies lowest in energy. If the outermost shell is more than half-filled, the level with the highest
va lue of is low est in energy.
These rules specify in a simple wa y how the usua l energy intera ctions dicta te the ground sta te
term. The rules a ssume that the repulsion betw een the outer electrons is very much greater than
the spin–orbit interaction which is in turn stronger than any other remaining interactions. This
is referred to as the LS coupling regime. Full shells and sub shells do not contribute to the quantum
numbers for tota l S, the total spin angula r momentum and for L, the total orbital angular
momentum. It ca n be shown that for full orbitals a nd sub orbita ls both the residua l electrostatic
term (repulsion betw een electrons) and the spin–orbit interaction can only shift all the energy
levels together. Thus when determining the ordering of energy levels in genera l only the outer
va lence electrons need to be considered.
23. Rules ca n be violated but Principle can’t be violated and have no exceptions at all.
24. 4S1
25. F  1 s²2 s²2 p5 Cl  [Ne]3s²,3p5 Br  [Ar]4 s²3 d10 4p5 I  [Kr]5 s²4 d10 5p5
26. Ionic bonds are formed by either loss or gain of electrons such as NaCl which is originally Na+Cl–
. Covalent bonds a re formed by sharing of electrons betw een tw o a toms. This sha ring may be
 
from same a toms or from different atoms such as H or O. If a toms a re same then bonds a re
purely cova lent but if atoms are different then such bonds are considered a s pola r cova lent.
Coordina te bond is also a type of covalent bond but here sharing of electrons takes place from a
single a tom such as compound of NH3 BF3 in which N shares its electron with B.
27. Most polar is KCl & least pola r is Cl2 .
28. The nega tive a nd positive ends of a pola r bond ma kes it a dipole. The polarity of the dipole is
indicated by the dipole moment (  ). The dipole moment of a bond is the product of magnitude
of the charge (e) on the atom (either the partia l positive cha rge or the partial nega tive charge
because they have the same magnitude) a nd the dista nce betw een the two cha rges (d). Dipole
moment is mea sured in a unit called Debye (D).
 = e× d
29. Forma l charge is the difference betw een the number of valence electrons an atom has w hen it is
not bonded to any a tom and the number of electrons it actually “ow ns” when it is bonded. An
atom “ow ns” a ll of its nonbonding electrons a nd ha lf of its bonding electrons.
Formal charge = No of valence electrons – (N o of non bonding electrons + ½ No of bonding
electrons)
Oxygen has 6 valence electrons but “own” electrons of oxygen in H3 O+ is 5 (2 non bonding plus
3, ha lf of six bonding). As the number of number of “own” electron is 1 less tha n its va lence
electron so its formal charge is 1.
30. Lewis structures of formic acid, formaldehyde and methanol are respectively
O O H H
C C CO
H
H O H H H H
Formic acid Formaldehyde Methanol
31. If there wa s a full negative charge on the oxygen a tom, the dipole moment would be
(4.80 × 10 -10 esu)×(1.22 × 1 0 -8 cm) = 5.86 × 10 -1 8 esu.cm = 5.86 D
Knowing that the dipole moment is 2.3 0 D, partial positive charge on oxygen atom will be 2.3 0/
5.86 = 0.39. From this we can conclude that oxygen ha s an excess of about 0.4 electron and carbon
atom has a deficiency of 0 .4 electrons.
32. Bond length of HX follows
HI (1 60 pm) > HBr (1 41 pm) > HCl (127 pm) > HF (9 2 pm)
 – HO  –  Br 
33. CH
3  Cl
–
, CH 
3  NH2
‚ , I   Cl – , CH
3  OH
–
, CH3–  Mg Br & NH 2   OH –
34. Ten organic compounds a re
SN Compound Use
CH3
Flavoring compound from the essential

01 OH
oil of spearmint
H3 C CH 3
Menthol
O CH 3
02 Perfume distilled from ja smine

CH 3

Cis Jasmone of jasmine
NH 2

03 Ba sis for the Dyestuffs industry
Aniline
OH
04 Antiseptic in surgery
Phenol
CH3
CH 3 CH 3
H3 C
05 Ma jor constituent of petrol
CH 3
Iso-octane
CH3 CH 3
H3 C CH 3 OH
06 For trea tment ofblindness
CH 3 Vitamin A
OH
HO O
07 HO OH Energy source for living organism
OH
Glucose
CH2 OH
H H O H HOH 2 C O H
O H HO Ordinary sugar isolated from sugarcane
08 HO OH H CH 2 OH
or sugar beet
H OH OH H
(Sucrose)
H2 C
N
HO
H 3C
09 Medicine used to trea t ma laria
N
Quinine
HS SH
10 H 3C CH3 Worst smell in the world

Propanedithiol
35. Functional group is an a tom or group of atoms in a molecule tha t gives the molecule its
chara cteristic chemical properties. The importa nce of functional groups lies in the fact that it is
 
the site of attack of reagent, makes families for organic compounds and helps in nomencla ture.
36. Alcohol, enol, phenol and carboxylic acid respectively
37. Bond line structures a re
O H3 CO
HO O OCH3
(A) (B) (C) H3 CO
O OCH3

O
O NH
+ O O O
(A) O N (B) O (C)
– O
O N
39. Proba ble formula s a re GeCl4 , AlH3 , CH2 Cl 2 , SiF4 & CH3 NH 2 , AlCl3 , CF2 Cl 2 , NI3 , PH3 .

40. Carbon ha s only four va lencies a nd donot have a ny va cant orbital so ca nnot expand its octet.
That’s w hy molecules with such structures are not possible at room tempera ture.
41. Non bonding electrons a re
× ×
×O ×
×O × × ×
×× × × ×O × CH 3
O ××
H3 C ××
CH 3 H3 C H3 C ××
× H3 C N ××
CH 3 Cl × H3 C O
×× ××

(A) (B) H 3 C – NH 2
O
(C) O (D) O
OH and H , and OH
H
NH 2
(E) N and N
NH2 , ,
Ionic bond
– +
43. H3 C O Na
Covalent bond
44. Homologue s a re the compounds with sa me general formula and possess simila r chemical
properties due to presence of sa me functiona l group (if any) i.e. all ca rboxylic a cids a re
homologues of each other starting from formic acid (HCOOH) to any carboxylic acid with formula
RCOOH where R is any acyclic sa turated a lkyl group. All alkanes sta rting from 1 carbon to
infinite ca rbon a re homologues. Homologues differ by (CH2 )n units.
 Homologues of Methane are Ethane, Propa ne, Buta ne & Pentane;
 Homologues of Formaldehyde (Metha nal) are Ethanal, Propa nal, Butanal and Pentana l;
 Homologues of Acetone a re Buta none, Penta none, Hexanone & Heptanone;
 Homologues of Formic a cid are Acetic acid, Propanoic acid, Butanoic a cid and Pentanoic
acid.
45. Molecules with single functional groups are considerd to be derived from a hydrocarbon by replacing
 
one of its H a toms w ith a functional group. If the hydroca rbon is a lipha tic then then the alkyl
group is represented by R, and the molecule containing functiona l group ma y be represented as
RG where G is functional group such as RCl for alkyl chloride, ROH for alcohol a nd RCOOH for
carboxylic acid.
46. Compounds in homologous series differ by (CH2 )n units w hich increases the siz e of a lkyl group,
so physica l properties changes gradua lly such as general increase in melting point, boiling point
is observed w ith decrea se in solubility in w ater. They undergo similar chemical reactions whose
ra te depends on the size of alkyl group and shape of molecule.
47. The w ord thio is usua lly used to indicate the presence of S. So sulphur a nalog of alcohol is thiol
& ether is thioether.
48. The functional groups present a re
(I) Thiol (II) Thiol & Ketone (III) Ether
(IV) Enyl halide (V) Imine (VI) Ether & Ketone
(VII) Ketone & Enol (VIII) Ether, Alcohol & 2° Amine (IX) Ether, Phenol & Aldehyde

(X) Imine (XI) Phenol
(XII) 1° Amine (XIII) Azo
(XIV) Alkene & Benzene (XV) Alkyl Benzene
(XVI) Peroxide (XVII) Amide, Thioether & Carboxylic acid
(XVIII) Amine & Imine (XIX) Ca rboxylic acid & Ester
(XX) Phenol & 2 ° Amide (XI) Amine, Amide, Ether & Sulphonamide
(XXII) Alcohol, Alkene & Ketone (XXIII) Amine & Ester
(XXIV) Amine & Alcohol, Imine (XXV) Alcohol, Ether, Enyl halide & Imine
(XXVI) Phenol & Aryl halide (XXVII) Amine, Ketone & Alkene
(XXVIII) Ether, Amine, Carboxylic acid & Sulphonamide
49. Structura l formula s for compound w ith such skeletons a re
H3 C H 3C
H3 C
(A) CH 2 (B) H3 C CH (C) Cl or CH 3
Cl
H 3C H3 C H3 C N
H3 C
(D) OH or CH 3 (E) H (F) CH 3 (G) H C
3
HO O O
50. There are of course many possible structures. A could be heteroa tom or a structural fra gment
while Ar could be any of a very large number of substituted benzene rings or even other types of
aroma tic rings. Four membered rings could have A = O, NH, CO, SO2 or even alkene while the
R1 & R2 could be same or different. To make such structure alw ays be careful that molecule must
follow octet rule. OCH 3
COOH Ph
CH 3 Ph OCH3
NH 2 OCH3
CH 3 CH 3 S
O HN H2 C O O O
The three a ryl groups in second example, all might be different or some might be same.
OH
CHO COOH
CHO OH O
 
O O
O O O
Cl N
OH
51. Total number of prima ry, seconda ry, tertiary and quaternary carbons a re
Com. Primary C Secondary C Tertiary C Quaternary C
I 3 1 1 0
II 7 0 3 1
III 4 2 2 0
IV 3 4 1 1
V 4 2 2 0
VI 4 3 1 0
VII 3 7 1 0
VIII 5 10 2 0
52. Total number of prima ry, secondary, tertiary hydrogens a re
Compound Primary H Secondary H Tertiary H
I 9 2 1
II 15 0 1
III 9 7 0
IV 9 8 1
V 8 4 1
53. Alicyclic compounds a re simply the cyclic a liphatic compounds (Cyclic + Alipha tic), w hich a re
commonly cycloalkane, cycloa lkene, cycloalkyne, cyclic ether, cyclic secondary a mines, cyclic
tertiary amine, cyclic ester, cyclic ketones, cyclic amide, cyclic acid anhydride.
54. Structures are
H CH 3 H CH3
O S O O + –
N N N N
(A) (B) (C) (D) (E) (G) (H) O O (I) O (J) O (L) (M)
(F) (K) O
CH 2 CH 2
55. (A) H3 C CH 3 (B) H C (C) H C
2 2
56. A. 109° 28´, sp3 B. 109 ° 2 8´, sp3 C. 109 ° 28 ´, sp3 D. 1 20° , sp2
sp3 sp 2
3
sp 2
H sp2 sp H H 3C sp sp3 H2 N COOH
H3 C 2
sp 2
C sp
CH 2 H2 C OH
57. sp 2 H sp2 H Cl CH 3 All sp 2 All sp 2 All sp 2
2 3
sp sp 2 sp
II sp 3 V VI VII
I III IV
NH 2 sp 2
.
CH 2 CH +2
CH3 CH 3 H
H3 C CH 3
sp 2 sp 2 CH –2
sp3 sp 2 sp2 N H3 C CH 3 H H
2 O HN sp 2 CH3 H CH 3
2 3
All sp All sp All sp2 sp
sp
3
sp3 S sp3 All sp2 All sp 3
All sp3
 
VIII IX (X) XI XII XIII XIV XIV
58. Overa ll sha pe of molecules a re
Com. Shape Com. Shape Com. Shape
I Planner II Non-Planner III Non-Planner
IV Planner V Non-Planner VI Non-Planner
VII Planner VIII Planner IX Planner
X Planner XI Planner XII Planner
XIII Planner XIV Planner XV Planner
59. Saturated and Unsaturated compound are
Comp. Nature Comp. Nature Comp. Nature
I Saturated II Saturated III Saturated
IV Unsaturated V Saturated VI Unsaturated

VII Unsaturated VIII Unsaturated IX Unsaturated
X Unsaturated XI Unsaturated XII Unsaturated
XIII Unsaturated XIV Saturated XV Saturated
60. Classifica tion of compounds a re
Com. Classification Com. Classification Com. Classification
I Non-aromatic II Aromatic III Anti-aromatic
IV Non-aromatic V Anti-aromatic VI Aromatic
VII Anti-aromatic VIII Non-aromatic IX Non-aromatic
X Anti-aromatic XI Aromatic XII Non-aromatic
XIII Aromatic XIV Aromatic XV Aromatic
XVI Non-aromatic XVII Aromatic XVIII Anti-aromatic
XIX Non-aromatic XX Aromatic XXI Non-aromatic
XXII Aromatic XXIII Aromatic XXIV Aromatic
XXV Aromatic XXVI Aromatic XXVII Aromatic
XXVIII Non-aromatic XXIX Aromatic XXX Aromatic
XXXI Aromatic XXXII Aromatic XXXIII Aromatic
XXXIV Aromatic XXXV Aromatic XXXVI Aromatic
XXXVII Aromatic XXXVIII Aromatic XXXIX Aromatic
XL Aromatic XLI Anti-aromatic XLII Anti-aromatic
XLIII Aromatic XLIV Aromatic XLV Aromatic
XLVI Aromatic XLVII Non-aromatic XLVIII Aromatic
XLIX Aromatic L Aromatic

 

Exercise
02 Objective Approach
Single Correct Questions (SCQ) :

1. First organic compound generated (1828) by Friedrich wohler is S
+ – 
(A) CO (B) N H O CN 4
(C) H 2 NCONH 2 (D) H 2 N - C- NH 2
2
2. Formation of large number of organic compound is due to
(A) size of carbon (B) Electronegativity of carbon
(C) Catenation property of carbon (D) Position of carbon in the periodic table
3. How many e– are used to make a single, double & triple bond
(A) 1,2,3 (B) 2,4,6 (C) 3,6,9 (D) 4,6,8
4. Electronegativity value on Pauling scale for C, H, N, O, F are
(A) 2.1, 2.5, 3.5, 4.0 (B) 2.5, 2.1, 3.0, 3.5, 4.0 (C) 2.5, 2.1, 3.5, 3.0, 4.0 (D) 2.1, 2.5, 3.5, 3.0, 4.0
5. Total number of bonds in the given compound H 2 C = C = CH - CH = C = CH 2 is :
(A) 9 (B) 15 (C) 14 (D) 16
 
6. Molecular formula of Phenantharene is :-
(A) C 14 H14 (B) C 14 H10 (C) C 14 H12 (D) C 12 H12
7. Number of sigma bonds in the given compound CH3 - CH2 - CH = CH - CN is :-

(A) 11 (B) 15 (C) 12 (D) 13
O
R –C–N S
8. Find the functional group which is absent in penicillin H
N
O COOH
Penicillin
(A) Amine (B) Amide (C) Thio ether (D) Carboxylic acid
9. Homologue of CH3 COOH is

(A) CH 3 COOCH 3 (B) CH3 COCH 2 OH (C) CH3 CH2 COOH (D) HCOCH 2 OCH3
10. Number of 1°, 2°, 3° & 4° carbons present in given compound respectively is
(A) 5, 2, 1, 0 (B) 5, 1, 1, 1 (C) 5, 1, 0, 1 (D) 5, 1, 1, 0
11. Number of 1°, 2°, 3° Hydrogens present in given compound respectively is
(A) 15, 2, 1 (B) 20, 2, 1 (C) 15, 4, 0 (D) 15, 4, 1
12. Number of 3° & 2° carbon atoms respectively in the following compound are -
(A) 5, 6 (B) 6, 6 (C) 5, 7 (D) 4, 7
OH
13. Number of 2° H atoms in the following compound is
(A) 7 (B) 5 (C) 6 (D) 4

14. Which molecule is considered as saturated one.
(A) Alkane (B) Alkene (C) Alkyne (D) Aromatic comp
15. Which molecule is considered as unsaturated one.
N
(A) (B) (C) (D)
O H
16. Central carbon in CH 2 = C = CH 2 will have which type of hybridization.
(A) sp (B) sp2 (C) sp3 (D) None
17. The given compound is

N CH 3
H
(A) Alicyclic heterocyclic (B) Unsaturated homocyclic
(C) Aromatic heterocyclic (D) Saturated heterocyclic

18. Which of the following is an alicyclic compound ?
(A) (B) (C)

O
 (D)
O
19. The saturated heterocyclic compound is –
(A) N (B) (C) (D)

H O
20. Which of the following do not have bridge head carbon in bicyclo compound.
(A) (B) (C) (D)
21. Which of the following is an unsaturated hydrocarbon.
(A) CH 3 - CH2 - C  N (B) CH 3 COCH 2CH3 (C) (D)

22. Which molecule is not planner in shape.
(A) (B) (C) (D)
23. Which molecule is heterocyclic in nature.

O
NH 2 OH O – C – CH 3
COOH
(A) (B) (C) (D)
N
24. Which molecule is anti-aromatic in nature.

+
(A) (B) (C) (D)
25. Which molecule is aromatic in nature.

+ +
(A) (B) (C) (D)
+
26. Which of the following alkane do not have any 2° carbon.
(A) (B) (C) (D)
27. Maximum angle strain is observed in

(A) Cyclopropane (B) Cyclobutane (C) Cyclopentane (D) Cyclohexane
Multiple Correct Questions (MCQ) :
28. Which statement is correct for element with single bond.
(A) Nitrogen have one lone pair of electron. (B) Oxygen have two lone pair of electron.
(C) Fluorine have three lone pair of electron. (D) Carbon have four lone pair of electron.
29. Which statement is correct for bond.
(A) Sigma bond is formed by axial overlapping of orbitals.
(B) Pi bond is formed by sidewise overlapping of p–p orbitals.

(C) Sigma & Pi bonds are a type of ionic bond.
(D) Co-ordinate bond is a type of covalent bond.

30. Which statement is correct for functional group.
(A) Functional group shows its characteristic chemical reaction.
(B) Functional groups helps in nomenclature of organic compounds.
(C) Functional groups serves to classify organic compound into different classes or families.
(D) All functional groups have same physical properites.
OH
HO O O
31. Functional group is present in vitamin C HO OH is:

Vitamin C
(A) Alcohol (B) Enol (C) Ester (D) Ether
32. Which functional group have absence  bond ?
(A) Alcohol (B) Aldehyde (C) Amine (D) Alkyl halide
33. Which functional group have  bond ?
(A) Ketone (B) Carboxylic acid (C) 3° amine (D) 2° amide
34. Which compound have C=N linkage ?
(A) Imine (B) Amine (C) Oxime (D) Hydrazone
O
EtO S N N CH 3
N
N O
35. Which functional group is present is Viagra N
N
O H (Viagra)
CH3
(A) Amide (B) Sulphonamide (C) Amine (D) Ester
H Cl O
36. Which functional group is present in sulpha drug O N S NH 2
O
COOH
(A) Sulphonamide (B) Carboxylic acid (C) Amine (D) Alcohol
37. Which compound(s) is/are homologue of CH3CH2CH2CHO ?
(A) CH2O (B) CH3CHO (C) CH3CH2CHO (D) CH3CH2COCH2CH3
38. Which statement is correct for homologues ?
(A) They have same type of chemical reaction. (B) They differ in (CH2 )n unit.
(C) They have same physical properties. (D) They are prepared by same general method.
39. Esters are formed by chemical reaction of
(A) Carboxylic acid & alcohol (B) Acid halide & alcohol
 
(C) Acid anhydride & alcohol (D) Aldehyde & alcohol
40. Which compound is unsaturated in nature ?
(A) (B) (C) (D)
41. Which compound is saturated in nature.
OH NH2 O Cl
(A) (B) (C) (D)
42. Which molecule have correct number of 2°C present.
H
OH
O N
(0)
(A) (3) (B) O O (C) (3) (D) N N (3)
HO OH H H

43. Which molecule have correct number of 2 H present ?
OH
NH2
(A) (10) (B) (9) (C) (8) (D) (8)
Cl
44. Which molecule will have Sp 3 hybridized carbon ?
+
O
(A) (B) (C) (D)
+ Cl
45. Which molecule is/are planner in shape ?
(A) (B) (C) (D)
46. Which molecules will exist at room temperature ?

O O
O
(A) (B) (C) (D)
47. Which molecule is/are polar in nature ?
(A) (B) (C) (D)
48. Which molecule is/are aromatic in nature ?
O HO O NC CN O
(A) (B) (C) (D)
HO O
49. Which molecule is/are aromatic in nature ?
(A) (B) (C) (D)

50. Which molecule have (  ) gamma position ? 
(A) +N (B) N (C) +N (D) + S
51. Which molecule with correct shape is mentioned ?
(A) Tub shaped (B) non-planner
(C) Planner (D) HC  CH Planner
52. The hybridizations of carbon atoms present in cumene is/are

(A) sp (B) sp2 (C) sp3 (D) dsp2

Assertion / Reason type Questions (A/R) :
Each question has 5 choice (A), (B), (C), (D) & (E) out of which only one is correct.
(A) Statement-1 is true, Statement-2 is true and statement-2 is a correct explanation for statement 1.
(B) Statement-1 is true, Statement-2 is true and statement-2 is not correct explana tion for
statement 1.
(C) Statement-1 is true and Statement-2 is false.
(D) Statement-1 is false, Statement-2 is true
(E) Both Statement-1 and Statement-2 is false.
53. Statement-1: The concept of ‘vital force theory’ was objected by Wohler by preparing urea from
NH4OCN.
Statement-2: ‘Vital force theory’ state that we can not prepare organic molecule in laboratory.
54. Statement-1: CH3CH2CH(NH2)CH3 is a secondary amine.
Statement-2: In 2° amine, –NH2 group attached with 2° C
55. Statement-1: (CH3)3COH is a tertiary alcohol.
Statement-2: In tertiary alcohol, –OH group is attached with tertiary carbon.
56. Statement-1: Oxalic acid & formic acid are homologue.
Statement-2: Homologues are those compounds which have same nature of chemical reaction and
differ in (CH2 )n unit.
57. Statement-1: have 1°, 2°, 3° & 4° carbon.
Statement-2: 1°, 2°, 3° & 4° carbon is that carbon which is attached with 1,2,3 & 4 other carbon
respectively.
58. Statement-1: Cyclohexane is saturated while cyclohexene is unsaturated.
Statement-2: Saturated compound is that which have only single bond while unsaturated compound
is that which have multiple bond of any form.
59. Statement-1: Hybridization of oxygen atom in furan is sp2.
60. Statement-1:
+
is a aromatic compound.

Statement-2: Hybridization is a mathematical approach to explain the shape of any atom in molecule.
Statement-2: Cyclic planner molecule with (4n + 2) electrons are called aromatic compounds.
61. Statement-1: Toluene is an alicyclic compound.
Statement-2: Alicyclic compounds are simply the cyclic aliphatic compounds.
62. Statement-1: Angle strain in decreasing order follows-
cyclopropane > Cyclobutane > Cyclopentane > Cyclohexane.
Statement-2: Angle strain is the half of angle difference between desired angle of sp3 atom and real
angle of the atom in cycloalkane.
63. Statement-1: Loss of one H from alkane leads to alkyl group.
Statement-2: Butane have four types of alkyl groups.
Match the Column type Questions (MTC) :
64. Match the compounds w ritten in Column-I with its nature in Column-II :-
Column - I Column - II
(A) (P) Aliphatic compound
(B) (Q) Aromatic compound

O
OCH 3
(C) (R) Saturated compound
(D) (S) Unsaturated compound

N
(T) Heterocyclic compound
6 5. Match the compounds w ritten in Column-I with its nature in Column-II :-
Column - I Column - II
(A) (P) Aliphatic
(B) (Q) Aromatic
(C) (R) Alicyclic
(D) (S) Heterocyclic

O
(T) Homocyclic
Comprehension type Questions :
Comprehension-01 :
 
Paracetamol is widely used as analgesic (pain reliever) & antipyretic (fever reducer) medicine. Based
on its structure, select the correct answer among this
H
N CH 3
HO O
Paracetamol
66. Functional group present in paracetamol is

(A) Alcohol (B) Amine (C) Ketone (D) 2° amide
67. Which statement is incorrect for paracetamol is
(A) Paracetamol is unsaturated compound. (B) Paracetamol is derivative of hydrocarbon.
(C) Paracetamol is heterocyclic compound. (D) Paracetamol is carbocyclic compound.

Comprehension-02 :
OH OH O N–OH
H 2 /Ni Cu NH 2 –OH H+ H2 O
Δ Δ + N Polymerization
Nylon-6
H
I II III IV O H
V
Based on this, answer the following questions.
68. Incorrect statement about above compound is
(A) A functional group present in II is alcohol. (B) A functional group present in III is ketone.
(C) A functional group present in IV is oxime. (D) A functional group present in V is lactone.
69. Incorrect statement about above compound is
(A) Compound I is saturated (B) Compound II is saturated
(C) Compound III is unsaturated (D) Compound IV is unsaturated
Integer type Questions :
70. Total number of primary carbon atoms present in is
71. Total number of aromatic compounds among the given molecule is
+
+
+
72. Total number of sigma bond () present in benzene is
73. Total number of homocyclic compounds among the given molecule is

OH O O
O
N S O HO OH
 


Exercise
03 World of competitions
1. In which of the following species is the underlined carbon having sp3 hybridisation ? [AIEEE-2002]
(A) CH3 COOH (B) CH3 CH 2 OH (C) CH 3 COCH 3 (D) CH 2 = CH - CH 3
2. The general formula C n H 2n O 2 could be for open chain [AIEEE-2003]
(A) carboxylic acids (B) diols (C) dialdehydes (D) diketones
3. Which one of the following does not have sp2 hybridized carbon ? [AIEEE-2004]
(A) Acetonitrile (B) Acetic acid (C) Acetone (D) Acetamide
4. Which of the following represents the given mode of hybridisation sp 2- sp2 -sp-sp from left to right ?
(A) H 2 C = CH - C  N (B) HC  C - C  CH [IIT-2003]
(C) H 2 C = C = C = CH 2 (D) H 2 C = CH - CH = CH 2
5. Which of the following molecules, in pure form, is (are) unstable at room temperature ? [IIT-2012]
O O
(A) (B) (C) (D)
6. The number of loan pair of electrons in melamine is [IIT-2013 (Advanced)]

(A) 4
 (B) 6 (C) 6

7. In allene (C3H4), the type(s) of hybridization of the carbon atoms is (are):
(D) 8
[IIT-2014 (mains)]
(A) sp and sp3 (B) sp2 and sp (C) only sp2 (D) sp2 and sp3
8. The number and type of bonds in C 2–

2
ion in CaC2 are: [IIT-2014 (mains)]
(A) One  bond and one  bond (B) One  bond and two  bond
(C) Two  bond and two  bond (D) Two  bond and one  bond
9. For the compounds CH3 Cl , CH 3 Br, CH 3 I and CH3 F , the correct order of increasing C-halogen bond
length is : [IIT-2014 (mains)]
(A) CH 3 F  CH3 Cl  CH 3 Br  CH 3I (B) CH 3 F  CH3 Br  CH 3 Cl  CH 3I
(C) CH 3 F  CH3 I  CH 3 Br  CH 3Cl (D) CH 3 Cl  CH 3 Br  CH 3F  CH 3I

10. Match the orbital overlap figures shown in List-I with the description given in List-II and select the
correct answer using the code given below the lists. [IIT-2014 (Advanced)]
List-I List-II
(P) 1. p-d  antibonding

Codes :-
(Q) 2. d-d  bonding P Q R S
(A) 2 1 3 4
(B) 4 3 1 2
(R) 3. p-d  bonding
(C ) 2 3 1 4
(D) 4 1 3 2
(S) 4. d-d  antibonding
1 2 3 4
11. In the compound H2 C = C = CH – CH 3 , the hybridization of 1 st and 2 nd carbon atom is: [BHU 2003]
(A) sp3-sp (B) sp3-sp3 (C) sp2-sp (D) sp2-sp2

12. Allyl cyanide contains  and  -bonds: [PMT (MP) 2004]
(A) 5 , 7  (B) 9 , 3 (C) 3, 4 (D) 9, 9
13. The C–H bond distance is longest in: [UGET (Med.) 2006]
(A) C 2 H2 (B) C 2 H 4 (C) C 2 H6 (D) C 2 H 2 Br2
14. The correct order regarding the electronegativity of hybrid orbitals of carbon is: [AIPMT 2006]
(A) sp < sp2 > sp3 (B) sp < sp2 < sp3 (C) sp > sp2 < sp3 (D) sp > sp2 > sp3
15. Number of  and π bon ds in C 6 H 5 COOH is: [DPMT 2007]
(A) 13 , 4 (B) 14, 4 (C) 15 , 4 (D) 16, 4

16. What is the percentage of p-character of hybrid orbits of carbon in methane, ethene and ethyne
respectively? [SCRA 2007]
(A) 75, 66, 50 (B) 50, 66, 75 (C) 25, 33, 50 (D) 50, 33, 25
(A) Acetone 
17. Compound which do not have sp2-hybridized C ?
(B) Acetic acid (C) Acetonitrile  (D) Acetamide
[JCECE 2008]
18. The state of hybridization of Carbon in 1, 3, 5 are H3 C – CH = CH – CH2 – C CH [CPMT 2008]

6 5 4 3 2 1
(A) sp, sp2 , sp3 (B) sp3 , sp 2 , sp (C) sp2 , sp, sp3 (D) sp, sp3 , sp2
19. Hybridization of N atom in pyridine is: [BHU 2008]

N
(A) sp3 (B) sp2 (C) sp (D) sp3 d
20. The number of π bonds in the following compound O 2 N – C  C – NO 2 is : [DPMT 2008]
(A) 2 (B) 3 (C) 4 (D) 1
21. Compound where underlined carbon use sp3 hybrid orbitals for bond formation is: [BCECE 2008]
(A) CH3 COOH (B) CH3 CONH 2 (C) CH3 CH 2 OH (D) CH 3 CH = CH 2
CH 3 CH3
22. The state of hybridiz ation of C 2 , C 3 , C 5 and C 6 of CH 3 – C – CH = CH – CH – C CH is in the
7 6 5 4 3 2 1
CH 3
following sequence [AIPMT 2009]
(A) sp, sp3 , sp 2 and sp3 (B) sp, sp2 , sp2 and sp3 (C) sp, sp2 , sp3 and sp2 (D) sp 3 , sp2 , sp 2 and sp
23. Increasing order of carbon-carbn bond length for the following [CET (karnataka) 2011]
C2H 4 C 2 H2 C6H 6 C2H 6

is :
(A) (B) (C) (D)
(A) B<C<A<D (B) C<B<A<D (C) D<C<A<B (D) B<A<C<D

24. Considering state of hybridization of carbon atoms, find out the molecule among the following which
is linear? [AIPMT 2011]
(A) CH 3 - CH = CH - CH 3 (B) CH 3 - C  C - CH 3
(C) H 2 C = CH - CH 2 - C  CH (D) CH3 - CH 2 - CH 2 - CH 3
25. Which one of the following is a non-benzenoid aromatic compound? [PMT (Kerala) 2011]
(A) Anthracene (B) Tropolone (C) Aniline (D) Benzoic acid
26. Only sp and sp2 hybrid orbitals are involved in the formation of [PMT 2012]
(A) CH 3 - CH = CH2 (B) CH3 - CH3 (C) CH3 - C  CH (D) H 2 C = C = CH2
27. The C–H bond and C–C bond in ethane are formed by which types of overlap? [CET 2012]
(A) sp3-s and sp3-sp3 (B) sp2-s and sp2-sp2 (C) sp–s and sp–sp (D) p–s and p–p
28. The radical
.
CH is aromatic because it has [NEET 2013]
2
(A) 6 p orbitals & 6 unpaired electrons. (B) 7 p orbitals & 6 unpaired electrons.
(C) 7 p orbitals & 7 unpaired electrons. (D) 6 p orbitals & 7 unpaired electrons.
29. Which compound has same hybridization as its combusion product CO2 ? [AIPMT 2014]
(A) Ethane (B) Ethyne (C) Ethene (D) Ethanol
(A)

30. Among the following aromatic compound is
(B) (C)
 (D)
[AIIMS 2015]


Answers
Objective Approach
02
01. (C) 02. (D) 03. (B) 04. (B) 05. (B)
06. (B) 07. (C) 08. (A) 09. (C) 10. (B)
11. (D) 12. (A) 13. (B) 14. (A) 15. (D)
16. (A) 17. (A) 18. (D) 19. (C) 20. (C)
21. (C) 22. (C) 23. (B) 24. (B) 25. (B)
26. (D) 27. (A) 28. (A,B,C) 29. (A,B,D) 30. (A,B,C)
31. (A,B,C) 32. (A,C,D) 33. (A,B,D) 34. (A,C,D) 35. (A,B,C)
36. (A,B,C) 37. (A,B,C) 38. (A,B,D) 39. (A,B,C) 40. (B,C,D)
41. (A,B,D) 42. (A,B) 43. (A,B,D) 44. (A,B,D) 45. (A,B,D)
46. (A,C,D) 47. (B,C,D) 48. (A,B,C) 49. (A,B,C,D) 50. (B,C,D)
51. (A,B,C,D) 52. (B,C) 53. (A) 54. (E) 55. (A)
56. (B) 57. (A) 58. (A) 59. (B) 60. (A)
61. (D) 62. (A) 63. (B) 64. (A-P,S ; B-P,R,T ; C-P,R ; D-Q,S,T)
65. (A-Q,T ; B-P,R,T ; C-P ; D-Q,S) 66. (D) 67. (C) 68. (D)
69. (A) 70. (4) 71. (6) 72. (12) 73. (6)
 


Answers
World of Competition
03
1. (B) 2. (A) 3. (A) 4. (A) 5. (B,C)
6. (B) 7. (B) 8. (B) 9. (A) 10. (C)
11. (C) 12. (B) 13. (C) 14. (D) 15. (C)
16. (A) 17. (C) 18. (D) 19. (B) 20. (C)
21. (C) 22. (A) 23. (D) 24. (B) 25. (B)
26. (D) 27. (A) 28. (A) 29. (B) 30. (A)

 

Approach
Objective Approach
02
1. Urea (H2 NCONH2)
2. Position of carbon in periodic table as it includes small size, electronegativity, catanation etc.
3. 2e– for single bond, 4e– for double bond & 6e– for triple bond.
4. Electronegativity of C, H, N, O, F are 2.5, 2.1, 3.0, 3.5 & 4.0 respectively.
5. Total no. of bond includes both  &  .
6. C4H10
7. 12 Sigma bond
8. Amine is absent.
9. Homologue of carboxylic is another carboxylic acid which differ in (CH2 )n unit.
10. 5, 1, 1, 1
11. For hydrocarbons 1°C, 2°C, 3°H have 3, 2, 1 1°H, 2°H & 3°H respectively.
12. 5 tertiary & 6 secondary C.
13. 2°H is that H which is present on 2°C.

14. Compound with only single bond is called as saturated compound.
15. Compound with any type of multiple bonds are called as unsaturated compounds.
16. sp

17. Alicyclic with heterocyclic nature.
18. Aliphatic cyclic compounds are called as alicyclic compound.
19. Saturated heterocyclic compounds are single bonded heterocyclic compounds.
20. Spiro compound do not have bridze head C.
21. Unsaturated hydrocarbons are having either C = C or C  C bond.
22. Cyclooctatetraene is non planner molecule.
23. Cyclic molecule having atleast 1 heteroatom (N, O, S) in ring are heterocyclic compound.
24. Cyclobutadiene is anti-aromatic.

25. Tropylium ion is aromatic in nature.
26. 2° Carbon is that carbon which is attached with 2 C atoms.
27. Cyclopropane has maximum angle strain.
28. N, O, F have 1, 2, 3 lone pair of e– but carbon do not have any lone pair of e– .
29. Sigma & pi bonds are an example of covalent bond.
30. Functional groups have different physical properties.
31. Alcohol, Enol & Ester.
32. Alcohol, amine & alkyl halide do not have  bond.
33. Ketone, Carboxylic acid & 2° amide have  bond.
34. Imine, Oxime & hydrazone have C = N bond.
35. Amide, Sulphonamide & amine are present in Viagra.
36. Sulphonamide, amine are present in sulpha drug.
37. Homologue of aldehyde is another aldehyde differ in (CH2 )n unit.
38. Homologue have different physical properties.
39. Esters are not formed by reaction of alcohol & aldehydes.
40. Compound with multiple bond is unsaturated.
41. Compound with only single bond is saturated in nature.
42. 2°C is that C which is attached with 2 C atoms.
43. 2°H is that H which is present on 2°C.
44. Sp3 hybridized carbon have 4  bonds.
45. Cyclooctatetraene is non-planner molecule.
46. Aliphatic & aromatic compound exist at room temperature but anti-aromatic compound do not exist
at room temperature.
 
47. Those molecules in which both ring become aromatic by breaking exocyclic double bond have
polarity.
48. A, B, C are aromatic by breaking exocyclic multiple bonds.
49. In case of polycyclic compound,  e– on peripheri is counted for (4n + 2)  e– .
50. Third position after functional group is considered as position.
51. Cyclooctatetraene is tub-shaped.
52. (Cumene)
53. No organic compound can be synthesized in lab is vital force theory.

54. Secondary amine are those compound in which 2 carbon atoms are attached with N.

55. Tertiary alcohol is that alcohol in which –OH group is attached with 3°C.
56. Oxalic acid & formic acid differ in CO2 unit.
57. 1°, 2°, 3°, 4°C is that carbon which is attached with 1, 2, 3 & 4 other carbon atoms.
58. Saturated compounds are single bonded while unsaturated compounds are multiple bonded.
59. Furan is planner so hybridization of O in it is sp2 .
60. Cyclopropenyl cation is aromatic.
61. Totuene is aromatic compound.
62. Angle strain for lower rings follows : Cyclopropane > Cyclobutane > Cyclopentane > Cyclohexane.
63. Loss of H from alkane give alkyl group so butane have 4 alkyl group- n-butyl, sec-butyl, iso-butyl &
tert-butyl.
64. Saturated compounds have only single bond while unsaturated compound have multiple bond.
Alicyclic compounds are also aliphatic in nature.
65. Homocyclic compounds are those in which each atom of ring is made up of C.
66. Functional group present in paracetamol is 2° amide.
67. Paracetamol have homocyclic ring as each atom of ring is made up of C.
68. Lactones are cyclic ester while Lactum is cyclic amide.
69. Saturated compounds are single bonded while unsaturated compounds are multiple bonded.
70. All terminal C is 1°C.
71. II, V, VI, VII, VIII & IX are aromatic.
72.  bond includes both C–H & C–C bond.
73. I, III, VI, VII, VIII & IX are homocyclic compounds.

 

Approach
World of Competition
1. Sp2 carbon have total 3  bond.

03
2. Carboxylic acid can have general formula CnH2nO2 as it have degree of unsaturation = 2.
CH3 – C  N CH3 COOH CH3COCH3 CH3 CONH2

3. Acetonitrile Acetic acid Acetone Acetamide
sp 2 sp2 sp sp
4. H2C=CH–C N
5. Anti-aromatic compounds are unstable at room temperature.
NH2
N N
6. (Melamine)
NH 2 N NH2
sp 2 sp sp2
7. H C=C=CH
2 2
Ca2+
8.
 
C C
9. Increasing order of C–X bond follows C–F < C–Cl < C–Br < C–I.
10. This question is based on overlapping of orbitals i.e. p & d orbitals.  bonds are formed by axial
overlapping while  bonds are formed by side wise overlapping. Bonding means overlapping of
similar orbital while anti-bonding means overlapping of dis-similar atomic orbital.
1 2 3 4
11. H2C=C=CH–CH
2
3
sp sp sp
2 3 sp
12. CH2 =CH–CH2 –CN is allyl cyanide.

13. C–H bond is longest when carbon is sp3 hybridized.
14. Electronegativity of hybrid orbital follows sp > sp2 > sp3 .
15. C6 H5 COOH is benzene carboxylic acid.

16. CH4 CH2=CH2 HC CH sp3 , sp2 , sp carbon have 75, 66, 50% p-character.
sp3 sp2 sp
CH3COCH3 CH3 COOH CH 3CN CH3 CONH2

17. Acetone Acetic acid Acetonitrile Acetamide
sp 3 sp2 sp2 sp 3 sp sp
18. CH3–CH=CH–CH2–C CH
6 5 4 3 2 1
19. N atom have 2  & 1 lone pair of e– so it has sp2 hybridization.
O O
20. –
C–C C–N
O O–
21. sp3 hybridized orbital have 4  bonds.
CH 3 CH3
sp3 sp3 sp2 sp 2 sp3 sp sp
22. CH –C–CH=CH–CH–C
7 3 6 5 4 3 2
CH
1
CH 3
°
1.54A °
1.34A °
1.20A
23. H3C CH3 CH2 CH2 °
1 .3 9A
HC CH
24. In compound having triple bond, 4 atoms are present in a line.
NH2 COOH
OH
25. O
Anthracene Tropolone Aniline Benzoic acid
 
sp 2 sp sp 2
26. H C = C = CH
2 2
H H
sp3 sp3
27. H C C H
sp 3–sp 3
H H s–sp3
28. Benzyl free radical is aromatic due to presence of benzene i.e. 6 p-orbital & 6 unpaired electrons.
29. CO2 H3C–CH3 HC CH H2C–CH2 CH3–CH2–OH

sp sp3 sp sp2 sp3
30. Cyclopropenyl cation is aromatic in nature.


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You are not alone there.........

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2 What is Organic Chemistry

What is Organic chemistry?

Animal fat NaOH Soap + Glycerin

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Py Py p-p sideways overlap

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Pentane Cyclohexane Benzene

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This H is shown because

end C have 3 H these C atoms must also carry O

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What makes the carbon so special?

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C – N– H 1 amine C – N– C 2 amine C – N– C 3 amine

R–O O–R R–O O–R R–O O–R H R

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Insert CH 2 unit Homologues

Insert CH2 unit Homologues

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CH2 =CHCH3  Cl–CH=CHCH3

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24 Learning is easy at www.CoachMe.co.in

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A. Linear shape B. Trigonal planner

sp3 sp3 sp2

Cyclooctatetraene = COT Overall Tub shaped

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10 Classification of organic compounds

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Examples of 6 pi electrons aromatic system:

Dimethyl fulvene Calicene

Tropylium ion + Substituted

Examples of heterocyclic 6 pi electron aromatic system:

Examples of 10 pi electrons aromatic system:

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Anthracene Phenanthrene Phenalenyl anion (14) Annulene

Cycloprop-2-enide ion Cyclobuta-1, 3-diene Cyclopenta-2,4-dienylium ion

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11 Baeyer’s strain theory

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Chair Half chair Twist boat Boat

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XIV XV XVI XVII XVIII XIX XX XXI XXII XXIII