CHM167/chapter8/HaslizaYusof

ORGANIC CHEMISTRY
8.1 Introduction

the organic compounds are devided into several groups known as homologues series
the homologous series is a series of organic compounds that have similar structural features but differ
from adjacent member by a (-CH2) group
each member of a homologous series has the same chemical properties and can be represented by a
general formula
Homologous Series

General Formula

Example

Functional Group

Alkanes

CnH2n+2
n = 1, 2, 3,.

CH4, n = 1

C C

Alkenes

CnH2n
n = 2, 3, 4,.

C2H4, n = 2

C C

Alkynes

CnH2n-2
n = 2, 3, 4,

C2H2, n = 2

C C

Alcohol

CnH2n+1OH
n = 1, 2, 3,.

CH3OH, n = 1

C OH

Carboxylic acid

CnH2n+1COOH
n = 1, 2, 3,

CH3COOH, n = 1

C COOH

Aldehyde

RCHO
R = alkyl group

CH3CHO, n = 2

Ketone

RCOR
R = alkyl group

CH3COCH3, n = 3

Primary amines

RNH2
R = alkyl group

CH3NH2

R C H

8.2 Hydrocarbons

hydrocarbon: compound that contain only carbon and hydrogen

have 4 categories: alkanes, alkenes, alkynes and aromatic compounds

O
R C R
H
R N
H

CHM167/chapter8/HaslizaYusof

8.3 Alkanes

alkanes are hydrocarbon containing only single bonds (CC)

also called saturated hydrocarbons because they are saturated with hydrogen

general formula: CnH2n+2, n = 1, 2, 3, .

the simplest alkanes: methane, where n = 1, C 1H2(1)+2 = CH4

the alkanes are named from the Greek numbers according to the number of carbon atom present

the suffix ane is added to the end of each name to indicate that the molecule identified is an alkane

8.3.1 Nomenclature

used the IUPAC (International Union of Pure and Applied Chemistry)

in this system, the longest continuous chain of carbon atoms called the parent chain- determines the
base name of the compound

the prefixes for the base names depends on the number of carbon atoms in the parent chain

base names for alkanes always have the ending ane

groups of carbon atoms branching off the base chain substituents

Table: Common Alkyl Groups
Condensed Structural Formula
Name
CH3

methyl
C2H5

CH2CH3 or

ethyl

fluoro

Cl

chloro

Br

bromo

iodo

CHM167/chapter8/HaslizaYusof

guide to naming alkanes:

STEP 1

Write the alkane name of the longest continuous

chain of carbon atoms
Number the carbon atom starting from the end nearest
a substituent
Give the location and name of each alkyl group
(alphabetical order) as a prefix to the name of the
parent chain (base chain)

STEP 2
STEP 3

Example:
CH3
CH3

STEP 1

CH CH2 CH2 CH3

Write the alkane name of the longest continuous chain of carbon atoms. In this
alkane, the longest chain has five carbon atoms, which is pentane
CH3
CH3

STEP 2

CH

CH2 CH2 CH3

pentane

Number the carbon atoms starting from the end nearest a substituent
CH3
CH3

CH CH2 CH2 CH3

2

STEP 3

pentane

Give the location and name of each substituent as a prefix to the alkane name.
Place a hyphen between the number and the substituent name
CH3
CH3
1

CH
2

CH2 CH2 CH3

3

2-methylpentane

List the substituents in alphabetical order

CH3 Cl
CH3

CH CH2 CH2 CH3

3 chloro 2 methylpentane

Use a prefix (di - , tri - , tetra -) to indicate a group that appears more than once. Use commas to separate
two or more numbers
CH3 CH3
CH3
1

CH CH2 CH2 CH3

2

2,3 dimethylpentane

When there are two or more substituents, the parent chain is numbered in the direction that gives the
lowest set of numbers
Br
CH3
5

CH3

CH CH2 C CH3
4

Br

2,4 dibromo 2 methyl pentane

CHM167/chapter8/HaslizaYusof

8.3.2 Drawing Structural Formulas for Alkanes

guide to drawing alkane formula

STEP 1

Draw the parent (main) chain of carbon atoms

STEP 2

Number the chain and place the substituents on the

carbons indicated by the numbers

STEP 3

Add the correct number of hydrogen atoms to give

four bonds to each carbon atom

Example:
Write the condensed structural formula for 2,3 dimethylbutane
STEP 1

Draw the main (parent) chain of carbon atoms. For butane, we draw a chain of
four carbon atoms and number it

C C C C
1

STEP 2

Number the chain and place the substituents on the carbons indicated by the
numbers. The first part of the name indicates two methyl groups (CH3-),
one on carbon 2 and one on carbon 3

CH3
C C C C
1

CH3
STEP 3

Add the correct number of hydrogen atoms to give four bonds to each carbon
atom

CH3

CH3 CH CH CH3
1

CH3

2,3 - dimethylbutane

CHM167/chapter8/HaslizaYusof

Exercise
1. Give the IUPAC name for each of the following
a) b)
F

CH3
CH3 C CH3

CH3 CH CH2 CH3

CH3

c)

d)

CH3 Cl
CH3

CH2

CH CH CH3

Br
CH3

CH2

e) CH3(CH2)5CH3
2. Draw a condensed structural formula for each of the following alkanes
a) 2 methylbutane
b) 3,3 dichloropentane
c) 2,3,5 trimethylhexane
d) 3 iodopentane
e) 2-methylpropane
f) 2-bromo-2,3-dichloropentane

Cl

CH CH2 CH CH3

CHM167/chapter8/HaslizaYusof

8.3.3 Isomers

same formula, different structure

the structural formulae of methane, ethane & propane can be written only in one way

that means, 3 hydrocarbons do not have isomers

a) alkanes with four carbon atoms

o

the hydrocarbon with molecular formula C4H10 has two isomers: butane & 2-methylpropena

H H H H
H C C C C H

CH3

H H H H

CH3 CH CH3

Butane
b)

2 methylpropane

alkanes with five carbon atoms

o
o

the molecular formula: C5H12

has 3 isomers: pentane, 2 methylbutane & 2,2 dimethylpropane

8.3.4 Reactions
Reagent
Bromine, Br2

Effect on alkanes
No effect in the dark. Bromine slowly decolourised in
sunlight. Halogenation reaction
H H

H C C H

Br2

H H

Chlorine, Cl2

uv
light

H Br
H C C H

HBr

HCl

H H

No effect in the dark. Reaction occurs in sunlight.

Halogenation reaction
H H
H C C H
H H

Cl2

uv
light

H Cl
H C C
H H

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8.3.5 Cycloalkanes

Molecular formula has two less H atoms than straight chain, CnH2n
H H
C
H C C H
H
H

cyclopropane

H H

H H
H
C
H C
C H
H

H C C H
H C C H
H H
cyclobutane

H C
C H
C
H
H
H H
cyclohexane

8.4 Alkenes

containing at least one double bond between carbon atoms ( C = C )

the simplest alkene is ethane, C2H4, also called ethylene

the suffix ene is added to the end of each name to indicate that the molecule identified is an alkene

CHM167/chapter8/HaslizaYusof

8.4.1 Nomenclature

guide to naming alkenes

STEP 1
Name the longest carbon chain with a double bond (C=C)
STEP 2

Number the carbon chain starting from the end nearest a

double bond

STEP 3

Give the location and name of each substituent (alphabetical

order) as a prefix to the name

Example:

CH3
CH3 CH CH CH CH3
STEP 1

Name the longest carbon chain that contains the double bond. There are five
carbon atoms in the longest chain. Replacing the corresponding alkane
ending with ene gives pentene
CH3

pentene

CH3 CH CH CH CH3

STEP 2

Number the longest chain from the end nearest the double bond. The number of
the first carbon in the double bond is used to give the location of the double
bond
CH3
CH3
5

STEP 3

2 pentene

CH CH CH CH3
4

Give the location and name of each substituent (alphabetical order) as a prefix to
the alkene name. The methyl group is located on carbon 4
CH3
CH3
5

CH CH CH CH3
4

4 methyl 2 pentene

Exercise
Give the IUPAC name for each of the following
1.

CH3
CH3

C CH2

2.

CH3
CH3

C C CH3
CH3

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8.4.2 Isomers

cis - and trans

1. 2-butene
a) cis 2 butene

b) trans 2- butane

2. 2,3-dichloro-2-butene
a) cis-2,3-dichloro-2-butene

b) trans-2,3-dichloro-2-butene

8.4.3 Reactions
1. halogenation
a) Br2

the decolorisation of bromine solution:

H H
H C C H

H H
+

Br2

H C C H
Br Br
1,2 - dibromoethane

Ethene
2. hydrogenation
H H
H C C H

H H
+

H2

H C C H
H H

8.4.4

Test to Confirm the Presence of the C=C

1. Bromine in CCl4
2. KMnO4 in acid
8.5 Alkyl Halide

containing the halogen elements (group 17); F, Cl, Br, I

example:
H H

H H

H H H H

H C C H

H C C H

H C C C C H

H Cl

H F9

Br H H H

CHM167/chapter8/HaslizaYusof

8.6 Alcohol

containing the hydroxide group, - OH

general formula: CnH2n+1OH
H

H C OH

R C OH

R C OH

primary alcohol, 1

secondary alcohol, 2

tertiary alcohol, 3o

8.6.1 Nomenclature
CH3

Example:
CH3

C CH2 OH
H

STEP 1

Name the longest carbon chain containing the OH group. Replace the e in the
alkane name with ol
CH3

CH3

C CH2 OH

propanol

STEP 2

Number the longest chain starting at the end closest to the OH group
CH3
CH3
3

STEP 3

C CH2 OH

1 - propanol

Name and number other substituents relative to the OH group

CH3
CH3
3

C CH2 OH

2 methyl 1- propanol

CH3
CH3

CH CH CH3
OH

8.6.2 Reactions
1. Oxidation
H
H C H

H
+

O2

2. Reduction
O
H C H

H C OH

H
+

H2

H C OH

10
H

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3. Halogenation
CH3

CH CH3

OH
2 - propanol

HI

CH3

H2O

I
2 - iodopropane

Hydrogen
iodide

8.7 Aldehyde

CH CH3

have carbonyl group (

add the ending al

general formula: R C H

) bonded to a least one H atom

8.7.1 Nomenclature
STEP 1

Name the longest carbon chain containing the carbonyl group by replacing the e in
the alkane name with al.
No number is needed for the aldehyde group because it always appears at the end
of the chain

STEP 2

Name and number any substituents on the carbon chain by counting the carbonyl
carbon as carbon 1
CH3

CH3 O
CH3
3

CH3

CH C H
2

2 methylpropanal

8.7.2 Reactions
1. Oxidation
H

H C OH

O2

H C H

2. Reduction
O
H C H

H
+

H2

H C OH
H

11

CH CH2 CH2 C H
4

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8.8 Ketone

have a carbonyl group (

add the ending one

general formula:

) on the interior of the chain

O
R C R

8.8.1 Nomenclature
STEP 1

Name the longest carbon chain containing the carbonyl group by replacing the e in
the alkane with one

STEP 2

Number the parent chain starting from the end, nearest the carbonyl group. Place
the number of the carbonyl carbon in front of the ketone name (propanone and
butanone do not require numbers)

STEP 3

Name and number any substituents on the carbon chain

O
CH3

C CH3

CH3

CH3

CH2 C CH3
butanone

propanone

CH2

CH3
1

3 - methylbutanone

CH C CH2 CH3
2

1. Oxidation

OH

O
+

2 bromo 3 - pentanone

8.8.2 Reaction

CH3 CH CH3

Br O

C CH CH3
2

3 - pentanone

O CH3
CH3

C CH2 CH3

O2

CH3

12

C CH3

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8.9 Carboxylic Acid

O

containing a carboxyl group

add the ending ioc

general formula:

C OH

O
R C OH

8.9.1 Nomenclature
STEP 1

Name the longest carbon chain containing the carboxyl group and replace the e
of the alkane name by oic acid

STEP 2

Number the carbon chain beginning with the carboxyl carbon as carbon 1

STEP 3

Give the location and names of substituents on the parent chain

O

CH3 O

H C OH

CH3

Methanoic acid
8.9.2

CH C OH

2 methylpropanoic acid

Reaction

1. Oxidation
H
CH3 C OH

O
+

O2

CH3

13

C OH

CHM167/chapter8/HaslizaYusof

TUTORIAL 8

1. Draw the structural formula for each of the following organic compounds
a)
b)
c)
d)
e)
f)
g)
h)
i)
j)
k)

2-methylpropane
2-bromo-2,3-dichloropentane
3-methyl-2-hexene
cis-2-butene
2,2,3-trimethylpentane
1-bromo-1-chlorobutane
2-methyl-2-butene
propanal
2,4-heptadiene
2-propanol
2-methyl-2-butanol

2. Draw and name all alkane isomer of the compound with molecular formula of C 5H12
3. Name of the following compound
a) CH3(CH2)5CH3
b) CH3CH(OH)CH2CH3
c) CH3CH2CH2CHO
4. Write the structures of the cis and trans isomers for the 2 butene.
5. Give one test to confirm the presence of the C=C bond in hydrogen.
6. Draw structures containing four carbon atoms for each of the following classes of compound:
a)
b)
c)
d)
e)

Alkane
Alkyl halide
Alcohol
Alkene
Carboxylic acid

7. Write the condensed structures and the IUPAC names for all five possible alcohols with general
formula C5H12O.
8. Identify the functional group of each of the following compounds
a)

CH3CH2COCH2CH2CH3

b)

CH3CH2CH2CHO

c)

CH3CH2COOH

d)

CH3CH2CH CH2

e) CH3CH2CH2OH

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f) CH3CH2CH3
9. Predict the product of each of the following reactions
a)
b)
c)
d)
e)

CH3CH2CH=CH2 + Br2 ___________

CH3CH2CH3 + Cl2 __________ + HCl
CH3CHO + H2 ___________
CH3COCH2CH3 + H2 _____________
CH3CH2CH2CH2OH + O2 _______________ + H2O

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