JC1 / H2 Chemistry

Chapter 2. Introduction to Organic Chemistry

2.1 Functional Group and Homologous Series
Functional group is an atom or group of atoms common to a series of organic compounds that determines
the principal chemical properties of the series

Homologous series is a series of compound with the same functional group but differ in their formulae by
the length of carbon chain (-CH2-). Members in the same homologous series:
1. have the same functional group
2. exhibit similar chemical properties
3. can be prepared by similar methods
4. can be represented by a general molecular formula, e.g., C nH2n+2 for alkanes
5. differ in formulae by a constant unit of -CH2- from the previous and next member
6. exhibit a gradual change of physical properties such as melting point or density, as Mr increases

Common homologous series

Homologous General formula Functional group Example
series Structural formula Name
Alkane CnH2n+2 - CH3CH3 ethane
Alkene CnH2n, n ≥ 2 >C=C< H2C=CH2 ethene
Alcohol R-OH -OH CH3CH2OH ethanol
Ether R-O-R R-O-R CH3CH2OCH2CH3 ethoxyethane/
diethyl ether
Aldehyde ethanal

Ketone propanone

Carboxylic acid ethanoic acid

Acyl chloride ethanoyl chloride

Ester ethyl ethanoate

Primary Amide ethanamide

Nitrile ethanenitrile

Primary amine R-NH2 -NH2 CH3CH2NH2 ethylamine

Halogenoalkane R-X -X CH3CH2Cl chloroethane

R1 refers to R group, which can be alkyl groups (CH 3-, CH3CH2-), phenyl group (benzene ring), etc.
Alkyl groups are derived from alkanes by the removal of a H atom, and have the general formula of C nH2n+1

Page 1 of 8
 JC1 / H2 Chemistry

2.2 Nomenclature and IUPAC naming

Nomenclature, or the systematic naming of chemical compounds, consists of prefix-stem-suffix.
(IUPAC naming)
Stem indicates:
1. Number of carbon atoms in the longest continuous chain in the carbon skeleton
No. of C atoms 1 2 3 4 5 6 7 8 9 10
Stem Meth- Eth- Prop- But- Pent- Hex- Hept- Oct- Non- Dec-

2. Type of bonding in the carbon skeleton

Letters after stem Indication
‘an(e)’ only contains C-C single bonds
‘en(e)’ contains C=C double bond
‘yn(e)’ contains C≡C triple bond

Suffix gives the principal functional group of the organic compound, and a number (locant) may be added
to show the position of the functional group. If there are more than one functional group, the functional
group with the highest priority is named in the suffix.
Priority Functional group
Highest Carboxylic acid
Ester
Acyl chloride (Acid halide)
Amide
Nitrile
Aldehyde
Ketone
Alcohol
Amine
Lowest
Alkene

Prefix denotes the substituent, an atom or group of atoms substituted in place of a hydrogen atom on the
parent chain of a hydrocarbon, present in the compound. If there are more than one substituent, they are
placed in alphabetical order and if the same substituent is present more than once, multipliers such as di-,
tri-, tetra-, etc. are added to the prefix. Numbers (locants) may be added to show the position of the
substituents if necessary
Substituent Prefix
-CH3 Methyl
-CH2CH3 Ethyl
-Cl, -Br, -I Chloro, bromo, iodo

Steps to determine IUPAC nomenclature

1. Identify the longest continuous carbon chain
2. Identify the functional group with the highest priority
3. Number the carbon chain, giving priority to the identified functional group
4. Consider the substituents
(Minimise the sum of locants and account for alphabetic order of substituents)

Page 2 of 8
 JC1 / H2 Chemistry

Example 1: Name the below compound according to IUPAC naming conventions.

1. The longest continuous carbon chain contains 4 carbon atoms, and hence the stem is but-.
2. There are carboxylic acid and alcohol functional groups, and carboxylic acid has the highest priority. The
suffix of the compound is -oic acid.
3. Thus, the right-most carbon atom can be considered as the first carbon atom.
4. There are two methyl substituents at the second carbon atom, hence the multiplier ‘di-’ is used.

Hence, the name of the compound is 4-hydroxy-2,2-dimethylbutanoic acid.

Example 2: Name the below compound according to IUPAC naming conventions.

1. The longest continuous carbon chain contains 6 carbon atoms, and hence the stem is hex-.
2. There is only one functional group, alkane. Since the compound is cyclic, its suffix is cyclo -ane.
3. There are methyl and ethyl substituents, and since ethyl group has a higher priority, the carbon atom
bonded to ethyl group is assigned first position.

Hence, the name of the compound is 1-ethyl-3-methylcyclohexane.

2.3 Formulae of Organic Compounds

Organic compounds can be represented using different types of formulae.
Formula Structural Displayed Stereochemical Skeletal
Description Shows how the Shows a detailed Shows the spatial Is derived from
atoms are structure showing arrangement of structural formula
connected to each the relative placing atoms, groups, and by removing C
other in the of atoms and their bonding using atoms, H atoms,
molecule, to give an number of bonds solid lines, and and C-H bonds.
unambiguous between them. Ring wedge and dash. Skeletal structure
structure. Brackets structures are only contains
are often used to represented using carbon-carbon
indicate substituent skeletal structure bonds and
groups. instead. functional groups.
Example: CH3CO2H,
Ethanoic acid CH3COOH, or

Page 3 of 8
 JC1 / H2 Chemistry

Example 3: Draw the structural, displayed, stereochemical, and skeletal formulae of 3-chloro-
2hydroxybutanal.
Formula Structural Displayed Stereochemical Skeletal
CH3CH(Cl)CH(OH)CHO,
C4H7ClO2, or

2.4 Isomerism
Isomerism is the existence of different compounds with the same molecular formula but different structural
or spatial arrangement of atoms. Constitutional isomerism occurs when molecules share the same
molecular formula but have different structural formulae. Stereoisomerism occurs when molecules share
the same molecular formula but have different spatial arrangement of atoms.

Isomerism

Constitutional
Stereoisomerism
isomerism

Functional group
Chain isomerism Cis-trans isomerism Enantiomerism
isomerism

Positional isomerism

Chain isomers differ in the structure of their carbon skeleton. They have similar chemical properties but
different physical properties. For example, C5H12 can be pentane, 2-methylbutane, or 2,2-dimethylpropane.

pentane 2-methylbutane 2,2-dimethylpropane

Positional isomers have the same functional group at different positions. They have similar chemical
properties but different physical properties. For example, C3H7OH can be propan-1-ol or propan-2-ol

propan-1-ol propan-2-ol
Page 4 of 8
 JC1 / H2 Chemistry

Functional group isomers have different functional groups. They have different physical and chemical
properties. Alcohol and ether, aldehyde and ketone, carboxylic acid and ester, and alkene and cycloalkane
are functional group isomers.
CH3CH2OH CH3OCH3
C2H6O
ethanol (alcohol) methoxymethane / dimethyl ether (ether)
CH3CH2CHO CH3COCH3
C3H6O
propanal (aldehyde) propanone (ketone)
CH3CH2COOH CH3COOCH3
C3H6O2
propanoic acid (carboxylic acid) methyl ethanoate (ester)
CH2=CHCH3
C3H6
propene (alkene) cyclopropane (cycloalkane)

Cis-trans isomerism occurs when there is:

1. restricted rotation about a carbon-carbon bond, e.g., C=C double bond in alkene.
2. there are two different groups bonded to each carbon with the restricted bond
In alkenes, cis-isomer has two identical groups on the same side of the double bond, while trans-isomer
has two identical groups on different side of the double bond.

cis-but-2-ene trans-but-2-ene

cis-pent-2-ene trans-pent-2-ene

Cis-trans isomerism is also found in cyclic compounds. However, the smallest cycloalkene that can exhibit
cis-trans isomerism is cyclooctene because when number of carbons < 8, the trans ring is too strained to
exist. Cycloalkanes with substituents can exhibit cis-trans isomerism.

Enantiomerism occurs as a pair of chiral compounds. Enantiomers have same physical properties but
different interactions with other chiral molecules. A chiral object has non-superimposable mirror image,
whereas an achiral object has superimposable mirror image.

In the context of organic compounds, a molecule is chiral if it:

1. has at least one chiral carbon atom bonded to 4 different groups
the chiral carbon is denoted by an asterisk (*)
2. has non-superimposable mirror image
3. does not have any plane, axis, or centre of symmetry

Page 5 of 8
 JC1 / H2 Chemistry

mirror plane

When drawing enantiomers, the molecules should be drawn using wedge and dash diagram, symmetrical
about the mirror plane.
Chiral molecules are optically active and hence rotate plane-polarised light (light that only vibrates in one
direction). Enantiomers rotate plane-polarised light in equal amounts, but in opposite (+ and -) directions.
Racemic mixture, or racemate, containing equimolar amount of both enantiomers does not rotate plane-
polarised light as rotating capacities of the enantiomers cancel out one another.
Enantiomerism can also occur in cyclic compounds if the rings are asymmetrical.

Meso compounds are molecules that contain two or more chiral centres but are achiral due to interior plane,
axis, or centre of symmetry.

meso-tartaric acid tartaric acid tartaric acid

mirror
plane

For compounds with more than one stereocentres, which are chiral carbons and C=C double bonds that can
exhibit cis-trans isomerism,

m: number of chiral carbons

n: number of C=C double
maximum number of stereoisomer = 2m+n bonds that can exhibit cis-
trans isomerism

Example 4: Find the number of possible chain isomers of C6H14

6C chain:

5C chain:

4C chain:
Hence, there are 5 chain isomers of C6H14

Page 6 of 8
 JC1 / H2 Chemistry

Example 5: Find the number of possible positional isomers of C3H6ClBr

Position of Br Position of Cl Compound

1 1

1 2

1 3

2 1

2 2

Example 6: Identify whether the following can exhibit cis-trans isomerism. If the molecule cannot exhibit
cis-trans isomerism, give a reason

(a)
No. Carbon-2 is bonded to two methyl groups.

(b)
Yes.

(c)
No. Trans-cyclohexene is too strained to exist.

Page 7 of 8
 JC1 / H2 Chemistry

Example 7: Find the number of chiral centres in the below molecule.

9.

Example 8: Find the number of chiral centres in the below molecule.

4.

Example 9: Calculate the number of possible stereoisomers of the below molecule and draw them.

There is one chiral centre and one C=C double bond that can exhibit cis-trans isomerism. Hence the number
of stereo centre is 2, and number of stereoisomers = 2 2 = 4.

trans

cis mirror plane

Page 8 of 8