Module

Code
Subject

JAMB

Universi

JAMB

Chemistry

ty
Unit

Topi

c
Lesson

Organic compounds

Name
Short

Aromatic Hydrocarbon, Alkanols , Alkanals and Alkanones. Alkanoic acids and Amines

Name
ID Name

Sathyakala.C

Date Of

14.1.2016

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20

Learning
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Aromatic Hydrocarbon, Alkanols , Alkanals and

Alkanones. Alkanoic acids and Amines

Audio
V1.1

V1.2

In this lesson, the

learner will be
able to:
o Explain the
properties
of benzene
distinguish the
various classes of
alkanols

TOS

In this lesson, the learner will be

able to:
o Explain the properties of
benzene

distinguish the various classes of

alkanols

V1.3

differentiate
between alkanals
and alkanones

differentiate between alkanals and

alkanones

V1.4

Explain the
various types of
alkanoic acids;

Explain the various types of

alkanoic acids;

V1.5

Explain the
properties of
alkanoates

Explain the properties of

alkanoates

Define the various

classes of amine

Define the various classes of

amine

V1.6

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V2.1

Introduction
Once upon a time, smell
was one of a chemist's best
tools.
Aromatic compounds are
important in industry.
They are extracted from
complex mixtures obtained
by the refining of oil or by
distillation of coal tar, and
are used to produce a
range of important
chemicals and polymers,
including styrene, phenol,
aniline, polyester and
nylon.

Let us discuss about

aromatic
hydrocarbon,
alkanoic acids and
their derivatives this
lesson.

Aromatic
hydrocarbon
are used to
produce a
range of
important
chemicals and
polymers

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3
Aromatic Hydrocarbons
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V3.1

Aromatic hydrocarbons

V3.2

Aromatic hydrocarbons are

also known as arenes.
Aromatic compounds
containing benzene ring are

TOS

Aromatic
hydrocarbons are
also known as
arenes

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Label:
Benzene
Toluene
Naphthalene
Biphenyl
a) The structure of
benzene a
planner ring
system in which
all bond angles
are 120
b) Two structural
formulas
implying that
the structure of
benzene is a
combination of
them both
together.
c) The common
representation

known as benzenoids and

those not containing a
benzene ring are known as
non-benzenoid.

V3.3

of benzene

Benzene is the simplest

aromatic hydrocarbon.
Benzene was isolated by
Michael Faraday in 1825.
In 1845, benzene was found
in coal-tar by Hofmann, and
this is still a source of
benzene and its derivatives.
Benzene was first
synthesised by Berthelot
(1870) by passing acetylene
through a red-hot tube.

Benzene was
isolated by
Michael Faraday
in 1825

Benzene is often depicted as

a 6-carbon ring with
alternating single and double
bonds, however
measurements of bond
length indicate that all six
bonds are equal and that
bonding electrons are shared
equally between the six

Benzene is often
depicted as a 6carbon ring with
alternating single
and double
bonds

carbons.

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Preparation Of Benzene
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V4.1

Preparation of benzene:

Decarboxylation of
aromatic acids:

Wurtz-Fittig reaction:

Friedel-Craft's reaction :

V4.2

Decarboxylation of aromatic
acids: Sodium salt of
benzoic acid on heating with
sodalime gives benzene

Sodium salt of
benzoic acid on
heating with
sodalime gives
benzene

V4.3

Wurtz-Fittig reaction:
When a mixture of aryl
halide and an alkyl halide is
treated with metallic sodium

Halide is reacts with

metallic sodium
benzene is formed

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the derivatives of benzene

are formed.

V4.4

Friedel-Craft's reaction :
Benzene reacts with alkyl
halides in presence of
anhydrous aluminium
chloride as catalyst to form
alkyl benzenes

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Benzene reacts with

alkyl halides in
presence of catalyst
to form alkyl
benzenes

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Physical Properties
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V5.1

Physical properties:
Some are liquids at room
temperature while others are
crystalline solids.
Most are non-polar because
of the symmetrical shape.
Insoluble in water.
Volatile.
Carcinogenic.

Physical properties:

Some are liquids at

room temperature
while others are
crystalline solids
Most are non-polar
because of the
symmetrical shape
Insoluble in water

Volatile
Carcinogenic

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Chemical properties
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V6.1

Chemical properties

Description
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Nitration:

Sulphonation:

Halogenation:

11

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Label:
Nitrobenzene
Chloro benzene
Fuming sulphuric acid
Benzene sulphonic acid

V6.2

V6.3

Nitration:
When benzene is heated with
a mixture of concentrated
nitric acid and concentrated
sulphuric acid nitro benzene is
obtained.

Sulphonation:

Aromatic compounds react

with concentrated sulphuric
acid to give arene sulphonic
acid.
V6.4

12

Halogenation:
Arene can be halogenated
with chlorine and bromine in
the presence of Lewis acid to
yield halo arene.

Benzene is heated
with conc. nitric
acid and sulphuric
acid nitro benzene
is obtained
Aromatic
compounds react
with concentrated
sulphuric acid to
give arene
sulphonic acid
Arene reacts with
chlorine in the
presence of Lewis
acid to yield halo
arene

V6.5

Benzene is used as a solvent

for the extraction of fats and
oils.
It is used as fuel along with
petrol.
It is used for the production of
maleic anhydride.

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Alkanol
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Benzene is used as
a solvent for the
extraction of fats
and oils

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V7.1

Alkanol

Monohydric Alkanol:

Dihydric alkanols:

Trihydric alkanols

V7.2

14

Alkanol common name is

Alcohol.
Alcohols are aliphatic organic
compounds that contain
hydroxyl groups. They can be
synthesized by a wide range
of methods, and the hydroxyl
group may be converted to
other functional groups. The

Alcohols are
aliphatic organic
compounds that
contain hydroxyl (OH) groups

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structure of an alcohol
resembles the structure of
water where one of the
hydrogen atoms of water is
replaced by alkyl group.
In IUPAC nomenclature, the
terminal "e" of the alkane is
replaced by "ol".
V7.3

Alkanols which contain only

one hydroxyl group per
molecule are called
monohydric alkanols.

V7.4

Alkanols which contain two

hydroxyl groups per molecule
are called dihydric alkanols.

V7.5

Alkanols which contain three

hydroxyl groups per molecule
are called trihydric alkanols.

15

Monohydric
alkanols contain
only one hydroxyl
group per molecule
dihydric alkanols
contain two
hydroxyl groups
per molecule
Trihydric alkanols
contain three
hydroxyl groups
per molecule

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Alkanols Classification And Properties
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V8.1
Alkanols
classification and
properties:

Classification:

Chain isomerism :

Position isomerism:

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Classification
Chain isomerism
Position isomerism
Functional isomerism

Functional isomerism:

V8.2

17

Alkanols can be
further classified as
primary, secondary
They are classified into
and tertiary
primary, secondary and
according to the kind tertiary alkanol
of carbon to which
the OH group is
linked.

V8.3

Boiling point of
primary alkanols
increases with
increasing length of
carbon chain.

Boiling point of primary

alkanols increases with
increasing length of
carbon chain

V8.4

Simple alkanols are

soluble in polar
solvents like water.

Simple alkanols are

soluble in polar
solvents like water

18

V85

19

Alkanols exhibit
three kinds of
isomerism.

Alkanols exhibit three

kinds of isomerism.

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Alkanols preparation:
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V9.1

Alkanols preparation:

TOS
Methanol preparation

Ethanol preparation

V9.2

20

Simple Alkanols are

obtained from natural
Methanol is obtained
sources.
from the liquid formed
Thus methanol is obtained
by the destructive
from the liquid formed by
distillation of wood
the destructive distillation of
wood so it is called wood
spirit.

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V9.3

Ethanol is manufactured by
the fermentation of sugar
present in grains and fruits
and hence called grain
alcohol.

Ethanol is
manufactured by the
fermentation of sugar

V9.4

Other alcohols can be

prepared by using addition
reaction or substitution
reaction.

Other alcohols can be

prepared by using
addition reaction or
substitution reaction

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Methods Of Distinction Between Three Classes Of Alcohols
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V10.
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22

Methods of distinction between

three classes of alcohols

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V10.
2

23

Lucas test:
An equimolar mixture of zinc
chloride and hydrogen
chloride is called lucas reagent.
When alcohol treated with Lucas
reagent to form alkyl chloride.
The alcohol is protonated by
Lucas reagent, and H2O group
attached to carbon is replaced
by the nucleophile Cl, which is
present in excess. Tertiary
alcohols react immediately.
Secondary alcohols react within
five or so minutes. Primary
alcohols do not react with Lucas
reagent at room temperature. It
requires high temperature.

When alcohol treated

with Lucas reagent to
form alkyl chloride

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Methods Of Distinction Between Three Classes Of
Alcohols
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V11.
1

Primary alcohol

Secondary alcohol

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Primary alkanols
are first oxidised to
the aldehyde which
undergoes further
oxidation to produce
the alkanoic acid

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equation

Tertiary alcohol

When Vo says The

oxidation of a
secondary alkanol
produces ketone.
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equation
When VO Says
Tertiary alkanols
cannot be oxidized.
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equation.
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sync with VO.

25

V11.
2

Oxidation:
Oxidation of alkanols with
acidified potassium dichromate
gives different oxidation
products.
Primary alkanols are first
oxidised to the aldehyde which
undergoes further oxidation to
produce the alkanoic acid.
The oxidation of a secondary
alkanol produces ketone.
Tertiary alkanols cannot be
oxidized.

V11.
5

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Oxidation of
alkanols with
acidified
potassium
dichromate
gives different
oxidation
products

Primary alkanols
are oxidised to
produce alkanal
(aldehyde)
The oxidation of
a secondary
alkanol
produces an
alkanone
(ketone)
Tertiary alkanols
cannot be
oxidized

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Methods Of Distinction Between Three Classes Of
Alcohols
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V12.
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V12.
2

Victor Meyers test:

In this test, the following steps

are involved:
(i) Alcohol is reacted with conc.
HI or red phosphorus and
iodine to form the
corresponding alkyl iodide.
(ii) Alkyl iodide is treated with
silver nitrite when
corresponding nitroalkane is
formed.
(iii) Nitro alkane is treated with
nitrous acid and the solution is
made alkaline by addition of
excess of caustic soda.

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n No
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Alkanal And Alkanone

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Alkanal And Alkanone
V13. Alkanal And Alkanone
1

V13.
2

V13.
3

In aldehydes the carbonyl group

is at the end of the carbon
chain and has a hydrogen atom
attached to it.

TOS

In ketones the carbonyl group is

joined to two other carbons.

V13.
4

Aldehydes ad ketones are

similar in that both types of
compound contain the carbon
group and are obtained by
oxidation of alcohols.

V13.
5

Aldehydes are readily further

oxidized whilst ketones are not

29

An alkanal
(aldehyde) has a
carbonyl group at
the end of the
carbon chain
An alkanone
(ketone) has a
carbonyl group
within the carbon
chain
Alkanal and
alkanone are
obtained by
oxidation of alcohol

Aldehydes are
readily further
oxidized whilst

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ketones are not

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Distinguish Aldehydes And Ketones.
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V14.
30

Distinguish Aldehydes And

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Ketones.

V14.
2

Several oxidizing agents can

be used to distinguish
aldehydes and ketones.

Oxidising Agent

Text
Aldehydes

Acidified
dichromate

orange
green

Benedicts
reagent

blue orange

Tollens reagent

colourless
silver

Acidified
potassium
dichromate
solution Will
change from
orange to blue or
green

Benedicts
solution Blue
precipitates turns

Acidified potassium
dichromate solution Will
change from orange to blue
or green. This is due to the
dichromate ion being reduced
chromium 3+ ion.

V14.
3

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Benedicts solution or Felings

solution.
Blue precipitates turns
orange to red

This is due to the copper 2+

ions being reduced to copper
1 oxide
V14.
4

Tollens reagent:
Changes from colourless
solution to silver mirror.
This is due to the silver +
ions being reduced to silver.

orange to red

V15.
5

32

Tollens reagent
Changes from
colourless
solution to silver
mirror

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Alkanoic Acids

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V15.
1

Alkanoic acids.:

V15.
2

The Alkanoic acids or

carboxylic acids are a
homologous series of

33

TOS

The Alkanoic acids

contain the same

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organic compounds.
They all contain the
same functional group
COOH
V15.
3

Carboxylic acids These

are represented by the
general formula RCOOH. IUPAC name is
derived by replacing
the terminal "e" of the
alkane name with "oic
acid". These
compounds are further
classified into monoand di-carboxylic
acids.

34

functional group
COOH

The names of
carboxylic acids end
in -oic acid eg
ethanoic acid

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V16.
1

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Methods Of Preparation Of Carboxylic Acids

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TOS
Methods of preparation Oxidation of primary alcohols
of carboxylic acids:
It is prepared from
RCH2OH + K2Cr2O7 RCOOH
alcohols, aldehydes,
Grignard reagents
Carbonation of Grignard reagents
RMgX + CO2 RCO2MgX +
H+ RCOOH

35

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Properties Of Carboxylic Acid

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Properties of carboxylic
acid:
Calcium carbonate +
Ethanoic acid Calcium
ethanoate + water +
Carbon dioxide

Ethanol + Ethanoic acid

Ethyl ethanoate +
Water

V17.
2

Carboxylic acids have

the following
properties:
1.

37

They dissolve in
water to produce

Carboxylic acids
dissolve in water to
produce acidic
solutions

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acidic solution.
V17.
3

They react with

carbonates to produce
carbon dioxide and a
salt and water

V17.
4

They all react with

alcohols, in the
presence of an acid
catalyst, to form
esters.

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Alkanoates
Bulletin Label
V18.
1

38

Alkanoates

They react with

carbonates to
produce carbon
dioxide and a salt
and water
They react with
alcohols to form
esters

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Examples of Sources
and Uses of Alkyl
Alkanoates

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Sources and Uses of

Alkyl Alkanoates

V18.
2

Esters are the derivatives of

the carboxylic acids in which
the OH part of the carboxylic
group has been replaced by
OR group where, R may alkyl or
aryl

Esters are generally

derived from a
carboxylic acid and an
alcohol.

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Amines
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V19.
1

39

Amines

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V19.
2

V19.
3

V19.
4
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Amines are
compounds
derived from
ammonia by
replacing one or
more hydrogen
atoms by alkyl or
aryl group.
Amines are
classified as
primary,
secondary and
tertiary amines.
When one of the
hydrogen atoms
in ammonia is
replaced by alkyl
or aryl group, it
is primary
amine.
.
If two hydrogen
atoms of amino

Amines are aliphatic and

aromatic derivatives of
ammonia

Primary amines compounds that

have only one group attached
to the nitrogen atom

Secondary amines compounds

that have two groups attached

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SUMMARY
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group are
replaced by alkyl
V20.1
Aromatic
or aryl groups, it
compounds
is a secondary
containing
benzene
amine.
are known
as
V19. ring
If three
hydrogen
benzenoids
5
atoms are and
those
not containing
replaced
by alkyl
aor
benzene
ring are
aryl groups,
it
known
as
nonis tertiary amine.
benzenoid

to the nitrogen atom

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Summary

Aromatic compounds
containing benzene ring are
known as benzenoids and
those
not containing
a
Tertiary
amines compounds
that
benzene
ring
are
known
as
have three groups attached to
non-benzenoid
the nitrogen atom

V20.2

Alcohols are
aliphatic organic
compounds that
contain hydroxyl
groups

Alcohols are aliphatic

organic compounds that
contain hydroxyl (-OH)
groups

V20.3

Alkanal and
alkanone are
obtained by
oxidation of alcohol

Alkanal and alkanone are

obtained by oxidation of
alcohol

V20.4

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