Summaryintrotoorganicchem 130116004352 Phpapp01

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Carbon forms a huge number of compounds.
The study of the structures, reactions and
properties of these carbon-based compounds
is called organic chemistry.
Note:
Carbon monoxide, carbon dioxide, metal
carbonates and metal cyanides are not classified
as organic compounds.
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Tetravalent
Carbon forms four bonds.
Strong CC bonds Due to strong CC bond, it
CC bonds are much stronger can bond with itself to form
than bonds between atoms of stable straight or branched
other elements. chains, or ring structures.
Bond Bond energy

/ kJ mol1
Bonding Nature
CC 350
of Carbon
SiSi 222
Multiple bonds
NN 160
OO 150 Carbon can also form
single, double or triple
bonds with itself.
Carbon compounds can
3 have varying degree of
unsaturation.
Organic Compounds
Aliphatic Aromatic
Saturated Contains one
Unsaturated or more
benzene rings
Open-chain Alicyclic Cl
Straight-chain (closed ring)
O
OH
Branched chain
Organic compounds in the same Example: alkene
homologous series:
possess the same general formula CnH2n
differ from the previous member in the CH2=CH2, CH2=CHCH2H,
series by a CH2 group CH2=CHCH2CH3, CH2=CHCH2CH2CH3
possess similar chemical properties, Alkenes possess a carbon-carbon
due to the presence of same functional double bond.
group Alkenes undergo electrophilic
addition reactions.
show gradual change in physical Ethene b.p. = 102 C
properties due to increased molecular Propene b.p. = 48 C
size and mass, caused by longer 1-Butene b.p. = 6.5 C
carbon chains 1-Pentene b.p. = 30 C
A functional group is an atom or a group of
atoms that governs the chemical properties
of an organic molecule.
Class of compound Functional group Name of functional group
RCH2OH Primary alcohol
RR1CHOH Secondary alcohol
Hydroxy compounds
RR1R2COH Tertiary alcohol
C6H5OH Phenol
RCHO Aldehyde
Carbonyl compounds
RR1CO Ketone
where R, R1, R2 represent alkyl groups, CnH2n+1
Class of compound Functional group Name of functional group
Carboxylic acids RCO2H Carboxylic acid
RCOCl Acyl chloride
Carboxylic acid
RCO2R1 Ester
derivatives
RCONH2 Amide
RNH2 Primary amine
Amines RR1NH Secondary amine
RR1R2N Tertiary amine
Nitriles RCN Nitrile
9 where R, R1, R2 represent alkyl groups, CnH2n+1

The structural formulae of organic
compounds may be represented using
displayed formulae
condensed structural formulae
skeletal formulae
Note that any structural formula given must
give an unambiguous structure.
E.g. 1-propanol
CH3CH2CH2OH
C3H7OH
10
Displayed Formulae
Show both the relative placing of atoms and the
number of bonds between them.
All bonds between atoms must be shown.
Exception:
The following convention for representing the
aromatic ring is preferred:
11
Condensed Structural Formulae
Each carbon atom is written separately.
Following each of these carbon atoms,
the other atoms that are bonded to this carbon atom
are written.
Substituent groups that are bonded to this carbon
atom are enclosed in brackets.
Similarly, the following convention for
representing the aromatic ring is preferred:
12
Skeletal Formulae
Simplified representation derived from a
structural formula by removing hydrogen atoms
(and their associated bonds) and carbon atoms
from alkyl chains, leaving just the carbon-carbon
bonds in the carbon skeleton and the associated
functional groups.
The following convention for representing the
aromatic ring is preferred:
13
IUPAC Nomenclature is a system of naming
chemical substances developed by the
International Union of Pure and Applied
Chemistry (IUPAC).
The IUPAC sets global standards for names,
symbols, and units used in chemical sciences.
16
The IUPAC name for an organic compound
consists of the following parts:
No. of carbon atoms in
Nature of
longest continuous carbon
parent chain
chain, i.e. parent chain
Prefix(es) Infix Root Suffix(es)
1 suffix + 2 suffix
Side chains & functional
groups of lower priority
Degree of
saturation or
unsaturation Functional group of
17
highest priority in
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Locants indicate
positions of
sustituent groups,
bonds etc. in
molecule
3-ethyl-4-methylhexane locant 3-oxohexanal
side-chains & infix root 1 suffix 2 suffix

functional groups of lower (nature of (no. of carbon atoms (degree of (main functional group,
priority, arranged in parent chain) in parent chain) saturation) of highest priority)
alphabetical order
locant 3-methylcyclopentene locant 2-hydroxypropanoic acid
2
1
3
18
(Source: http://en.wikipedia.org/wiki/IUPAC_nomenclature_of_organic_chemistry)
Locants indicate positions of root 1 suffix

sustituent groups, bonds etc. in (no. of carbon atoms (degree of
molecule in parent chain) saturation)
18-bromo-12-butyl-11-chloro-4,8-diethyl-5-hydroxy-15-methoxytricos-6,13-diene-19-yne-3,9-dione
tricos 23 carbons
side-chains & 2 suffix
functional groups of lower priority, (main functional group,
19
arranged in alphabetical order of highest priority)
Punctuation rules:
Di-, tri- etc. are not taken into consideration
when arranging side-chains and functional
groups alphabetically.
Commas are placed between numbers.
Hyphens are placed between a number and a
letter.
All parts are connected either by merging
successive names, including commas or hypens
to form a one-word name.
20
Functional groups control the chemistry of
organic molecules.
They contain reactive sites:
Electron deficient sites
E.g. a carbon atom bonded to a more
electronegative bromine atom
Electron rich sites
E.g. a -system in an alkene or a benzene ring
21
Types of
Bond Fission
Heterolytic Homolytic
When a covalent bond between When a covalent bond between two
two atoms breaks, one of the atoms breaks, each atom retains one
atoms retains both the bonding bonding electron.
electrons to bear a negative Free radicals are formed.
charge. A free radical is an electrically neutral
The other atom bears a positive atom or group of atoms that has one
charge. unpaired electron. It is unstable and
highly reactive.
HCl H+ + Cl:
ClCl Cl + Cl
23
Types of
Reagents
Electrophile Nucleophile
A reagent that is attracted to A reagent that is attracted to
regions of negative charge regions of positive charge or
or high electron density electron deficient sites
An electron pair acceptor An electron pair donor
Good bases are generally
Positive ions: NO2+
good nucleophiles
+ end of an induced dipole: +BrBr
+ end of a permanent dipole: +HCl Negative ions: HO:, NC:
Neutral molecules: H2O:, :NH3
24
Isomers are molecules that have the same
molecular formula but different arrangement
of atoms in space.
Isomerism
Stereoisomerism
Structural isomerism
Same molecular formula
Same molecular formula Same structural formula
Different structural formulae Different spatial arrangement
of atoms in 3D space
Cis-trans
Chain Functional Positional isomerism
isomerism isomerism isomerism
25 Optical
isomerism
Chain Isomerism
Arises due to the different arrangement of carbon
atoms in a carbon chain.
E.g. isomers of hexane, C6H14
26
Positional Isomerism
Arises due to the different positions assumed by
a functional group on a carbon chain or ring.
OH
OH
OH
pentan-1-ol pentan-2-ol pentan-3-ol
CH3 CH3 CH3

Cl
Cl
2-chloromethylbenzene 3-chloromethylbenzene
Cl
4-chloromethylbenzene
27
Cis-trans (a.k.a. geometric) isomerism
[Use of E-Z nomenclature is not required by the
9647 syllabus.]
Criteria:
Restricted rotation about a double bond, e.g.
carbon-carbon double bond, or
Restricted rotation due to a rigid ring structure
Two different substituent groups attached to each
atom in a double bond, e.g. to each carbon atom in
a carbon-carbon double bond
29
Optical isomerism
Criteria:
A chiral carbon, i.e. an asymmetrical carbon atom
with four different substituent groups
No plane of symmetry
Optical isomers exist as a pair of non
superimposable mirror images of each other.
Optical isomers are also known as enantiomers.
32
Enantiomers
Identical chemical properties and physical
properties
Rotate plane of polarised light in opposite
directions
33
Racemic mixture
Equal amounts of both enantiomers.
Optically inactive, as there is no net rotation of
plane-polarised light. Although both enantiomers
rotate plane-polarised light in opposite
directions, the rotations cancel out.
34
Drawing optical isomers
Optical isomers must be drawn as three-
dimensional structures according to the
convention used in the example below:
35
(Source: Higher 2 Chemistry Syllabus 2013/9647)

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Bond Bond energy

where R, R1, R2 represent alkyl groups, CnH2n+1

9 where R, R1, R2 represent alkyl groups, CnH2n+1

Prefix(es) Infix Root Suffix(es)

3-ethyl-4-methylhexane locant 3-oxohexanal

side-chains & infix root 1 suffix 2 suffix

locant 3-methylcyclopentene locant 2-hydroxypropanoic acid

Locants indicate positions of root 1 suffix

CH3 CH3 CH3

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