CHEM 1012

Introduction to
Organic Chemistry
Lecture no. 1
Introduction

Giuseppe Pileio

Introduction to the course

About Me

Name: Giuseppe
Surname: Pileio
Nickname: Peppe
Location: 30/3047, School of Chemistry
E-mail: g.pileio@soton.ac.uk
Phone: 023 80 59 4146
Web: http://www.mhl.soton.ac.uk/~peppe
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About you
Please, write down on a piece of paper:

Name
Surname
E-mail
Your past experience in chemistry or science
Why did you choose that course?
What do you want to learn in this course?
What should I do to match your personal needs?
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Course plan: Topic already covered

Atomic and Molecular Structure:

Structure of the Atom
Basic equations
The Periodic Table
Ionic Compounds
Covalent bonding
Dative bonding

John
(Week 1-2)

Acids and Bases

Rates of Reaction
Energy, Entropy and Equilibrium

Iris
(Week 3-5)

Course plan: Topic to be covered here

Organic Chemistry

Reactions

Functional groups

Nomenclature

Physical Properties

Characterization
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Learning Outcomes
By the end of this course you will be able:
to Recognize organic molecules by their Functional Groups
to Identify them by their proper official name
to Know their main reactions and how they transform
to Understand and predict their physical properties
to Know how to characterize them
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textbooks
Introduction:
Chemistry, Rob Lewis and Wynne Evans, ISBN 0-333-962575
Catch Up Chemistry Mitch Fry and Elizabeth Page, ISBN 1904842119

Further and better Understanding:

Organic Chemistry, S. H. Pine, ISBN 0-07-100242-1

Lecture no. 1

Learning Outcomes
By the end of this lecture you will be able:
to Understand the meaning and importance of Organic
chemistry
to Understand the concept of functional groups
to Recognize the structure of alkanes
to Learn the rules of nomenclature and be able to call
molecules with their proper names
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What is Organic Chemistry?

A piece of matter that contains carbons bonded to
non-metals is called organic matter
Organic Chemistry is the chemistry of molecules containing
carbon bonded to non-metals (H, O, N, S etc)

Organic Chemistry studies the organic matter by

classification of known substances (functional groups,
nomenclature and characterization) and/or by the
discovery of new ones. It focuses also on how organic
matter evolves (reactions) and on its main features
(properties)
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Why it is so important?
It is the chemistry of the living matter!
All the living matter, Archaea, bacteria, Protista, Fungi,
Plantae, Animalia, are made by molecules containing
carbons!
Animalia,Plantae, Fungi

organs

quarks

tissue

atoms

cells

Archaea,
Bacteria,
Protista

molecules
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Some relevant example in biology: DNA

H
N H

N
R

H N

Me

N
R

O
A.T base pair

H
O

N
N
R

James Watson & Francis Crick

Nobel Prize for Medicine/Physiology 1962

N H

N
N

H
G.C base pair
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Some relevant example in biology: Krebs Cycle

Hans Krebs
Citric acid (Tri
Carboxylic Acid, TCA)
cycle
Nobel prize for
medicine/ physiology
1953
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Functional groups: a simplified list

In organic molecules there are special groups of atoms
that characterize them by giving them peculiar properties.
These groups are called functional groups.
Molecules that have the same functional groups have the
same properties and reactivity
Content

Chemical Class

Hydrocarbons

F, Cl, Br, I

Haloalcanes

Alcohols, Ketones, Aldehydes,

Carboxilate, Ether, Ester

Amides, Amines, Imines

Phosphine

Sulfoxide, Thiol

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Hydrocarbons
Content

Chemical Class

Hydrocarbons

Simplest class of organic molecules

They only contains C and H
They are divided in 3 main subclass:
Subclass
Alkanes
Alkenes
Alkynes

formula
CnH2n+2
CnH2n
CnH2n-2

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Alkanes
Content

Chemical Class

Formula

Hydrocarbons

CnH2n+2

n (Molecular formula)

Structural Formula

Name

C1H2*1+2=CH4

Meth-ane

Methane has 4 bonds,

which are sp3 hybridised

109.5o

C
H

H
H

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n (Molecular formula)

Structural Formula

C2H2*2+2=C2H6

C3H2*3+2=C3H8

Name
Eth-ane

Prop-ane

The radical CnH2n+1 is called alkyl

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Condensed structural furmulae

Condensed structural formulae are quite useful and are
intended to be used to save time and to make more clear
complex structures
They can be easily drawn following these rules:
1.
2.
3.
4.

Each segment represents a C-C bond

Each end-point represent a C
Protons (as much as allowed) are omitted
All the other atoms explicitly drawn

= C2H6

= C3H8 =

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n (Molecular formula)

Structural Formula

C4H2*4+2=C4H10

Name

But-ane

Butthere is another possibility!

C4H2*4+2=C4H10

Iso-But-ane

They are called branched Hydrocarbons

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Structural Isomerism
Isomers = two molecules with the same molecular formula
but different structural formula
n (Molecular formula)
C5H2*5+2=C5H12

Structural Formula

Name
Pent-ane
n-pentane
iso-pent-ane
neo-pent-ane
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Homologous series
Hydrocarbons that differ by -CH2 units
They are very important to know since they are the
basis for the nomenclature of organic compounds!
n
6
7
8
9
10

name
Hex-ane
Hept-ane
Oct-ane
Non-ane
Dec-ane

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12

Undec-ane
Dodec-ane

13
14
15
16
17
18
19
20

Tridec-ane
Tetradec-ane
Pentadec-ane
Hexadec-ane
Heptadec-ane
Octadec-ane
Nonadec-ane
Eicos-ane 22

Systematic Nomenclature: IUPAC rules

1. The longest continuous sequence of carbons is the
basis for the parent name.
Whole
Molecule

PARENT NAME

ROOT
(Meth, Eth, Prop)

ending
(-ane)

Meth-ane CH4
CH3CH3
Eth-ane
Prop-ane CH3CH2CH3

Fragments
PARENT NAME
ROOT
(Meth, Eth, Prop)

-yl

Meth-yl
Eth-yl
Prop-yl

CH3CH3CH2CH3CH2CH223

2. A secondary prefix is used to designate the structure of

the side chain
Side chain, 1 fragment, 1 C
Parent name = met-yl
Main chain, 3 carbons
parent name = prop-ane
parent name = Methylpropane
3. The position of the side chain is given by numbering the
main chain so that the side chain has the lowest number
parent name = 2-Methylpropane

2
1

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4. Multiple side chain are labeled with the appropriate

prefix (di-,tri-,tetra-)

Side chain, 1 carbon

Parent name = met-yl
2
1

4
3

6
5

Main chain, 6 carbons

parent name = hex-ane
Side chain, 1 carbons
Parent name = met-yl

parent name = 2,3-Dimethylhexane

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5. When two different fragment are attached they are

arranged alphabetically
Side chain, 1 carbon
Parent name = met-yl
2
1

4
3

6
5

Main chain, 6 carbons

parent name = hex-ane
Side chain, 2 carbons
Parent name = eth-yl

parent name = 3-Ethyl-2-Methylhexane

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6. When two different numbering sequences begin with the

same number, the lower number at the first point of
difference is preferred
Side chain, 1 carbon
Parent name = met-yl
2
1

4
3

6
5

Main chain, 6 carbons

parent name = hex-ane
Side chains, 1 carbon
Parent name = met-yl

First point
of difference

parent name = 2,3,5-trimethylhexane

not
2,4,5-trimethylhexane

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7. The primary prefix cyclo- is placed immediately before

the parent name if the structure is cyclic

2
1

4
3

hexane

6
5

cyclo-hexane

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What we learn in this lecture?

Carbon is the element that is central for life
Organic molecules are characterized by function
groups
Rules to follow for the nomenclature of organics
compounds
Hydrocarbons (Alkanes, Alkenes, Alkynes)
Condensed structural formula and structural
isomerism
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