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Functional groups
A functional group is an atom or a group of
atoms with characteristic chemical and
CHM 102: physical properties. It is the reactive part of
FUNCTIONAL GROUPS the molecule.
The chemistry of an organic molecule is
primarily determined by the functional groups
By it contains, not by its size or complexity.
Dr T. A. Afolabi Organic compounds are classified by the
presence of characteristic functional
groups.

Hydrocarbons
A functional group determines the Organic compounds containing only carbon and
following properties of a molecule: hydrogen are known as hydrocarbons.
bonding and shape There are several major groups of hydrocarbons;
type and strength of intermolecular Aliphatic hydrocarbons are primarily straight and
branched chains of hydrocarbons consisting of
forces
alkanes, alkenes, and alkynes.
physical properties When only single C––C bonds exist in a
Nomenclature hydrocarbon, it is called a saturated hydrocarbon.
chemical reactivity Unsaturated hydrocarbons contain at least one
double or triple bond.

Hydrocarbons ALKANES
H
H H
H H H
H C C H
C H C C C H
H H
Alkanes
H H H H H
Alkanes have only C – C single bonds (contains H
Ethane (CH3-CH3)
only C‐C & C‐H σ bond) and no functional group. Methane (CH4) Propane (CH3-CH2-CH3)
General formula: CnH2n+2 e.g. Ethane CH3‐CH3
Because their carbon atoms can be joined H H H H
together in chains or rings, they can be H C C C C H
H H H H H
categorized as alphatic (acyclic) or cyclic. H C C C C C H
H H H H
Cycloalkanes contain carbons joined in one or H H H
Butane (CH3-CH2-CH2-CH3) H H
more rings; they have two fewer H atoms than an Pentane (CH3-CH2-CH2-CH2-CH3)
acyclic alkane with the same number of carbons.

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Hydrocarbons
Alkenes have a C=C (double bond) as a
functional group. General formula: CnH2n e.g.
Ethene, CH2=CH2
Alkynes have a C C triple bond as a functional
group. General formula: CnH2n‐2
e.g. Ethyne HC CH
Hydrocarbons
Alkyl groups are a type of hydrocarbon formed
by removing a hydrogen atom from an alkane.
Their names are formed by using the alkane
prefix and attaching “yl.”
Alkyl are sometimes represented with the
symbol R.
The alkyl groups attach themselves to other
groups.
CH3‐ Methyl
C2H5‐ Ethyl

Hydrocarbons
Aromatic hydrocarbons are unsaturated cyclic
compounds that are resistant to addition reactions.
They derive their name from the distinctive odors
they exhibited when discovered.
Benzene is the most important aromatic compound.
Because most aromatic compounds are derived from
benzene, it can be considered the parent of other
aromatic compounds.

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Identify/name the following functional groups;

O O Naming Organic Compounds
C The IUPAC name of an organic compound is composed of
three parts.
R SR
R Cl

Prefix Root (Parent) Suffix

The name of every organic molecule has 3 parts:

R C N 1. The root/parent name indicates the number of carbons
in the longest continuous chain.
2. The suffix indicates what functional group is present.
3. The prefix tells us the identity, location, and number of
R–NH2 substituents attached to the carbon chain.

Naming Organic Compounds Functional Group Priority
1. Functional group: Identify the functional group(s) ‐ onium (R4N+, R4P+, R3O+, R3S+, R2X+) (is greater 
and know the Major/Main functional group.
2. Root/Parent: Find the longest carbon chain (it
than)  > carboxylic acid  (‐COOH) 
MUST include the carbon with the functional >  carboxylic anhydride  
group).
> carboxylic esters (‐COOR)   > acyl esters (‐RCOX)
3. Suffix: Identify the major functional group.
Replace ‐ane (in the alkane) with the appropriate > amides (‐CONH2)    >  nitriles (‐C= N) 
suffix.
4. Give a position number to every carbon atom in > aldehydes (RCHO)  >  ketone (RCOR)
the main chain; start from the carbon closer to the > Alcohols (ROH)       >  phenols (ArOH)
‘carbon containing the functional group’.
5. Prefix: Identify and name all the substituents > thiols (‐SH)     >   Amines (‐NH2)    
appropriately (indicate their position) >  Imines (=NH)  >  Hydrocarbons (‐C=C, C=C, C‐C)
6. Put the name together: prefix + root + suffix.

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Hydrocarbons [ ‐C=C‐ >  ‐C=C‐ >  ‐C‐C‐ ]

> ethers (‐OR)  >  Sulphides (‐SH)   >  Halides (‐X)   
>  Nitro  O >     Nitroso
N N O
O
>  Azides >       Diazo

N N N N N

These groups should be cited only as prefixes; they 
are regarded  as substituents on the hydrocarbon 
chains

Drawing organic structures
3 major ways of drawing organic structures are:

Di‐ or tri‐ is used in the prefix or suffix to indicate

the presence of two or three of the minor or
major functional groups (or substituents),
respectively.

Exercise 1 Exercise 2
Draw the following organic compounds in  1. Name the organic compound below:
Kekule, condensed, and skeletal form:
a) Methane to pentane (a)
b) Propene, 1‐ Butene, 
c) 1‐Pentene and 2‐Pentene
d) 2‐petyne and 2‐Hexyne Cl
e) 2‐Bromo‐3‐methyl‐1‐heptane (b)
f) Hexane to Decane

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Exercise 3
Name the following organic compounds:
ISOMERS
CH3
• Isomers are compounds that have the same 
formula but different structures. 
Cl • Isomers that differ in their connections among 
atoms are called constitutional isomers. 
CH3
• When atoms other than carbon and hydrogen 
CH3 are present the ability to have functional 
group isomers arises. 
• Isomers are molecules that, due to the 
Cl CH3
CH3 Cl
differences in their connections, have not only 
CH3
different structures, but belong to different 
families of organic molecules.

Constitutional Isomers CH3 Geometric isomers

C4H10 CH3CH2CH2CH3 CH3CHCH3

C
Cl
C3H7Cl CH3CH2CH2Cl
CH3CHCH3

CH3CH2OH CH3‐O‐CH3
C 2H 6O

27 28

Geometric isomers Exercise 4 Name the following isomeric  compounds

CH2CH3
H 3C CH2CH3 H
For disubstituted alkenes (with two substituents on C C C C
the double bond), alkenes can be named using the H H H3C H
cis–trans nomenclature:
 cis‐isomers have the substituents on the same
side
trans‐isomers have the substituents on the H
Br

opposite side. H H
H Br
Cis‐ and trans‐isomers are also called geometric Cl

isomers because they have different shapes. Cl

29 30

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2 2
C7H14 C7H14

cis- 1,2-dimethylcyclopentane
trans- 1,2-dimethylcyclopentane

31 32

Exercise 5 Exercise 6
Classify each pair of the following isomers (or 
otherwise).
1. Write the structural formulae of: 
(a)
(i) 2‐bromo‐3‐chloro‐3‐methylpentane      
and
(ii) 3‐ethyl‐4‐methylhexane                
(b)
(iii) 2‐methyl‐3‐ethylhexane 
and
(iv) 4‐ethylnonane
(v) 6‐ethyldecane
(c)
and
33

(2) Write the structural formulae of: Aromatics
(i) 2‐bromo‐3chloro‐3‐methylpentane       Monosubstituted derivatives are usually named 
(ii) 4‐ethyl‐2‐methylheptane        after benzene (C6H6),although some non‐
(iii) 2,2,5‐trimethyloctane  (iv)  2,3,4‐trimethylheptane. systematic or ‘trivial’ names (in brackets) are still 
(3) Name the following organic compounds used.
1 2
Br

CH3 CH CH CH CH CH3

CH3 Cl CH2 CH3

3 F
4 CH3

CH3 CH2 CH CH CH3

CH3
Cl

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The word benzene comes first when functional  Disubstituted derivatives are sometimes named

groups of higher priority (than benzene) are on  using the prefixes ortho (or positions 2‐ and 6‐),
the ring. meta (or positions 3‐ and 5‐) and para (or
position 4‐). For trisubstituted derivatives, the
lowest possible numbers are used and the
prefixes are arranged alphabetically.

Exercise 7 Name the following: Alcohols

General formula
C CH
CnH2n+1OH or R‐OH
CH3-CH-OH CH3CHCH3
ethanol C H 3 C H 2 C H 2 -O H
propan-1-ol OH
OH (or 1-propanol)
C H 3 C H 2 -C C -C CH propan-2-ol
(or 2-propanol)
CH3CHCH2CH3
CH3CH2CH2CH2-OH
CH3HC C-CH2CH C(CH3)2 OH
1-butanol
(or butan-1-ol) butan-2-ol
(or 2-butanol)

Esters Amides
These are named in two parts.
The R1 group is the prefix, and N– is written
before this to show that the group is on
nitrogen.

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Aldehyde Ketone
R‐CHO Alkanone:      RCOR 

O
CH3 O
Cl O
CH3CCHCH2CCH3
CH3CHCHCH2CH
O CH3CCH2CH2CH3
CH3 CH3
Br

Ethers: Name the simpler alkyl group + O atom as an

Simple ethers are usually assigned common names; alkoxy substituent by changing the ‐yl ending of
the alkyl group to ‐oxy.

CH2CH3 O CH3CH2 diethyl ether

Name the remaining alkyl group as an alkane,

More complex ethers are named using the with the alkoxy group as a substituent bonded to
IUPAC system. this chain.

Preparation of alkane
1. Wurtz reaction
Na R R
The Chemistry of 2R X

Alkane 2. Grignard reduction
R X + Mg RMgX
H2O
R H

3. Reduction
R X + Zn + H+
R-H + ZnX2
R X + LiAlH4 dry ether
RH + LiX + AlX3

4. Hydrogenation
H2
RC CR' RCH2CH2R'

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Sources of alkanes
Reaction of alkane
1. Combustion Alkanes are obtained from crude oil and natural
gas.
R + O2 CO2 + H 2O
Natural gas contains 60–90% methane.
2. Halogenation 
Crude oil is a mixture of many carbon
R + X R-X + HX compounds with different chain lengths.
Reactivity   X: Cl2 > Br
The oil is therefore separated into groups of
H:  3o > 2o > 1o > CH3‐H compounds with roughly the same chain length
3. Free radical substitution in an oil refinery.
R-H + X. R. + HX The technique that is used to refine the oil is
called fractional distillation.
R . + X2 R-X + X.

Fractional distillation of crude oil Fractionating column

 The oil is heated and passed into a tall fractionating
column.
 Compounds with large molecules and high boiling
points are collected at the bottom of the tower,
whereas the more volatile components, with smaller
molecules, are collected near the top.
 Each group of compounds collected is called a
fraction.
 Each fraction is still a complicated mixture, since it
contains alkanes of a range of carbon numbers and
isomers of each carbon number.
 In addition to alkanes, crude oil contains some
cycloalkanes and aromatic compounds – the
proportion of each present depends upon the source
of the oil.

Alkenes
 Alkene molecules contain a double bond 
between carbon atoms. 
The Chemistry of They have the general formula CnH2n and their 
names end in ‘ene’. 
Alkene The first three (ethene, propene, and butene) 
are gases at 25°C.
CH3CH2CH=CH2
H H H H
H 1-butene
C C C C C H

H H H H CH3CH=CHCH3
but-2-ene

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3. Dehydration of alcohol
Preparation of Alkene
acid
1. Dehydrogenation of alkylhalides C C
heat
C C + H2O

H OH

C C + KOH Alc
C C + HX

4. Reduction of Alkynes
H X R R
H2
Ease of dehydrogenation: 3o > 2o > 1o R-C C-R
C C
Pd or Ni-B
H
2.  Dehalogenation of vicinal dihalides.  cis
H
R
C C + Zn H
C C + ZnCl2 Na or Li
R-C C-R C C
X X NH3
H
R
trans

3. Addition of hydrogen halide.

Reactions of alkene
1. Hydrogenation
C C + HX C C

C C + Pt, Pd, or Ni H X
H2 C C
HX = HCl, HBr, HI
H H

2. Halogenation 4. Addition of sulphuric acid

C C + X2 C C
C C + H2SO4 C C
X X
H OSO3H
X2 = Cl2, Br2

5. Addition of water  8. Polymerisation
H+
C C + C C heat CH2
HOH
nCH2=CH2 * CH2 *
pressure n
H OH

6. Halohydrin formation
9. Hydroxylation
C C + X2 + H2O C C + HX

H OH
C C + KMnO4 or HCO2OH C C

X = Cl, Br OH OH

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Structure of ozone:
Ozonolysis
O
O
Ozonolysis or ozonation is the cleavage  O
O

O
O O
(+) O
O (-)

of an alkene by ozone (O3). Ozonolysis reactions

It is a cycloaddition that destroys bonds
1. O3 R
+ O
ozone is a powerful oxidant and cleaves  R
2. Me2S
O
R
aldehydes
R
the alkene to make two carbonyl  R O OH
1. O3
compounds. R
2. H2O2
+ carboxylic acids
R
Ozone s a 1,3‐dipole and does typical  OH O
R

1,3‐ dipolar cycloadditions with alkenes.  R

1. O3
R OH
2. NaBH4 alcohols
R + OH R

Alkynes

The Chemistry of General formula: CnH2n‐2

Presence of at least one triple bond

Alkyne HC CH HC
propyne
C CH3
ethyne
HC C CH2 CH3 HC C C CH3
but-1-yne
(or 1-butyne) but-2-yne
(or 2-butyne)

Preparation of alkynes Reaction of alkynes

Dehydrogenation of alkylhalide
H H
1. Hydrogenation
H
Pd or
C C + H2 C C
C C alc. KOH NaNH2
C C Ni-B
C C
H H
X X X

Dehalogenation of tetrahalides C C
Na or Li
C C
X X
H H

+ 2 Zn + 2 ZnX2
C C C C 2. Halogenation
X X
X X C C + X2 C C + X2 C C
Reaction of water and calcium carbide X X
X X
CaC2 + H2O HC CH + X = Cl, Br, 
Ca(OH)2

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3. Addition of hydrogen halide
H X
C C + HX C C + HX C C
H X
H X

4. Addition of water (hydration) General exercise

C C + H2O H2SO4 C C C C
HgSO4
H OH H O

(2) Name the following organic compounds Exercise 8

CH3
1. Write the structural formulae of: 
(i) 2‐bromo‐3‐chloro‐3‐methylpentane      
Cl
(ii) 3‐ethyl‐4‐methylhexane                
CH3
(iii) 2‐methyl‐3‐ethylhexane 
CH3
(iv) 4‐ethylnonane
(v) 6‐ethyldecane
Cl CH3
CH3 Cl
CH3

Exercise 9 2. Which of the following is an amide?

1. Which of the following is an ester? O O

O O

CH2CH3
H3CH2CH2C CH3 H3CH2CH2C N
H
H3CH2CH2C CH3 H3CH2CH2C NH2 A B
A B O O
O O

H3CH2CH2C H2N CH3 H3CH2CH2C OH

D
O CH3 H3CH2CH2C OH C
D
C

71 72

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Exercise 10
3 O 4
Name the following compounds:  O
CH3 O (CH3)2CHCH
1 C6H5CH=CHCH
CH3CHCHCH2CH

CH3

5 O O
2 O

CH2
HCCH2CH2CH2CH
CHCH2CH2CH2CH2CH

O Exercise 11
6 Give the IUPAC name of the following:
CH3CCHCH2CCH3
7
CH3 1 2
CH3 O

8 O 3 4

CH3CCH2CH2CH3
6
5

7 Exercise 12
Draw the structure corresponding to each IUPAC
name.
8 C l a. 3‐ethyl‐2‐methylhexane
b. 4‐butyl‐1,1‐diethylcyclooctane
c. 2,2,6,6,7‐pentamethyloctane
I d. cyclobutylcycloheptane
e. 3‐ethyl‐1,1‐dimethylcyclohexane
I

9
C l

13