ALKANOLS

Alkanols, formerly called alcohols are group of compounds containing the hydroxyl (–
OH) group. They form a homologous series with general molecular formula (GMF)
CnH2n+1OH where n is greater or equal to 1(n . The hydroxyl (– OH) group is the
functional group of the alkanols. The members of the alkanols include:

Molecular Name Boiling Structural formula

formula points

CH3OH Methanol -162 CH3OH

C2H5OH Ethanol -87 CH3CH2OH
C3H7OH Propanol -42 CH3CH2CH2OH
C4H9OH Butanol -0.5 CH3CH2CH2CH2OH
C5H11OH Pentanol 36 CH3CH2CH2CH2CH2OH
C6H13OH Hexanol 69 CH3CH2CH2CH2CH2CH2OH
C7H15OH Heptanol 98 CH3CH2CH2CH2CH2CH2CH2OH
C8H17OH Octanol 126 CH3CH2CH2 CH2CH2CH2CH2CH2OH
C9H19OH Nonanol 151 CH3CH2CH2CH2 CH2CH2CH2CH2CH2OH
C20H21OH Decanol 174 CH3CH2CH2CH2CH2 CH2CH2CH2CH2CH2OH

The simplest member of the series is methanol (CH 3OH), sometimes known as wood
spirit or carbinol. It is poisonous and could cause blindness if consumed. Ethanol is the
second member of the series and the most important.

CLASSIFICATION OF ALKANOLS

A. Classification based on the number of hydroxyl groups.

1. Monohydric Alkanols: They contain one hydroxyl group per molecule.

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 Example:
H H

H3C – C – OH H3C – C – CH3

H OH
ethanol Propan-2-ol

2. Polyhydric alkanols
i. Dihydric alkanols: They contain two hydroxyl groups in a molecule.
Example:
CH2OH
Ethane – 1, 2 - diol
CH2OH

ii. Trihydric alkanols: They contain three hydroxyl groups in a molecule.

Example
CH2OH

CHOH

CH2OH Propan – 1, 2, 3 – triol (glycerol)

B. Classification based on the number of Alkyl groups

i. Primary alkanols (1o): In this group, the carbon atom bearing the hydroxyl
group is attached to only one alkyl group and two hydrogen atoms.
Examples are:
H H

H3C – C – OH CH3 – CH2 – C – OH

H
OH Butan – 2 - ol
Propan – 2 - ol
ii. Secondary Alkanols (2o): In this group, the carbon atom bearing the
hydroxyl group is attached to two alkyl groups and one hydrogen atom.
Examples are:
H H
CH3 – C – C2H5
H3C – C – CH3

OH OH
Propan – 2 - ol Butan – 2 - ol
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 iii. Tertiary alkanols (3o): In this group, the carbon atom bearing the hydroxyl
group is attached to three alkyl groups examples are:
CH3
CH3
CH3 – C – C2H5
CH3 – C – CH3
OH
OH
2methylButan – 2 - ol
2-methylPropan – 2 - ol

NOMENCLATURE OF ALKANOLS
In naming alkanols, the longest chain containing the hydroxyl (-OH) group is chosen as
the parent alkanol. The suffix is –ol and the position of the substituent groups and the
hydroxyl group are indicated by number, the lowest number is assigned to the hydroxyl
group. Alkanols with two hydroxyl groups are named as diol while alkanols with three
hydroxyl groups are named as triol.

PREPARATION OF ETHANOL

Ethanol can be prepared in the laboratory by several methods:

1. Hydrolysis of iodoethane with an alkali.

2. Hydrolysis of ethyl ester with hot alkali.
3. Reducing ethanol with nascent hydrogen.
Industrially/commercially, ethanol is prepared by.
4. Hydrolysis of ethene.
5. Fermentation.

PREPARATION OF ETHANOL FROM ETHENE

Ethene is bubbled through concentrated tetraoxosulphate (VI) acid, H 2SO4 at 80oC under
pressure, ethyl hydrogen tetraoxosulphate (VI) is obtained which is then hydrolysed by
boiling with water to give ethanol on distillation.

C H ( ) + H SO ( )
C H HSO ( )

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C H HSO ( ) + H O( ) C H OH( ) + H SO ( )

PREPARATION OF ETHANOL BY FERMENTATION

Fermentation is the slow decomposition by microorganisms of large organic molecules

(such as starch) into smaller molecules (such as ethanol).

The starchy food (potatoes, cassava and cereals) is crushed and boiled to extract starch
granules. Malt is added to about 55 oC for one hour. Malt is added and the enzyme
diastase from malt converts starch to maltose.
diastase
2(C6H10O5)n(s) + nH2O(l) C12H22O11(aq)
Maltose

Yeast is then added at room temperature. The enzyme maltose from yeast converts
maltose to glucose.
Maltose
C12H22O11(aq) + H2O(l) 2C6H12O6(aq)
Glucose

Another enzyme zymase, also from yeast converts glucose to ethanol and
carbon(IV)oxide.
Zymase
C6H12O6(aq) 2C2H5OH(aq)+ 2CO2(g)
Glucose Ethanol

The ethanol produced is distilled to obtain about 95% pure ethanol.

THE BREWING PROCESS

Brewing is the process employed in the production of alcoholic beverages. Barley is

partially germinated to produce malt which is employed in the fermentation.

Beer can be made by fermenting sugar from salt and adding dry flower of the hop plant to
produce the characteristic flower. If the sugar comes from grape juice, the product is
wine. Distillation of wine produces brandy, while distillation of fermented grain produces
whisky.

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PHYSICAL PROPERTIES OF ETHANOL

1. It is a colourless, volatile liquid with a characteristic taste and smell.

2. It is readily soluble in water in all proportions.
3. It has a boiling point of 78oC.
4. It is neutral to litmus.

CHEMICAL PROPERTIES OF ALKANOLS

1. Combustion: Ethanol burns in air or oxygen with a pale blue flame yielding water
and carbon (IV) oxide.
C2H5OH(l) + 3O2(g) 3H2O(g) + 2CO2(g)
2. Reaction with sodium and potassium: Ethanol reacts with sodium at room
temperature to produce sodium ethoxide and hydrogen.
2C2H5OH(aq) + 2Na(s) 2C2H5ONa + H2(g)
Sodium ethoxide

3. Reaction with chlorides of phosphorus: Ethanol rigorously reacts with

phosphorus (V) chloride at room temperature, to liberate a steamy fume of
hydrogen chloride and chloroethane vapour.
C2H5OH(aq) + PCl5(l) C2H5Cl(g) + H2(g)
(Phosphorous oxotrichloride)
4. Oxidation: Ethanol under favourable condition is readily oxidized to ethanol by
warming with potassium heptaoxodicholomate (VI) solution which has been
acidified with dilute tetraoxosulphate (VI) acid. On further oxidation, ethanol is
converted to ethanoic acid in the presence of excess dilute tetraoxosulphate (VI)
acid.
C2H5OH(aq) + [O] K2Cr2O7
CH3CHO(g) + H2O(l)
from (ethanal)

CH3CHO(g) + [O] CH3COOH

(ethanoic acid)

Generally, primary alkanols are oxidized to alkanals and then carboxylic acids
while secondary alkanols are oxidized to alkanones and tertiary alkanols are not
oxidized.

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 O
CH3CHOH CH3 + [O] CH3-C-CH3 + H2O(l)

5. Esterification: Alkanols react reversibly with carboxylic acids in the presence of

mineral acid to form alkanoates (esters). The process is known as esterification.
Alkanol + acid ester + H2O e.g.
C2H5OH + CH3COOH CH3COOC2H5 + H2O
(ethyl ethanoate)
6. Dehydration: Dehydration is a process in which molecule(s) of water is/are
removed from a substance. With excess concentrated tetraoxosulphate (VI) acid at
180oC, ethanol reacts to form ethyl hydrogentetraoxosulphate (VI) which then
decomposes to yield ethene.
180oC
C2H5OH(aq) + H2SO4 C2H5HSO4(aq) + H2O(l)
o
C2H5HSO4(aq) 180 C C2H4(aq) + H2SO4(l)
H2SO4 excess

USES OF ETHANOL

1. Ethanol is a useful solvent used to dissolve perfumes, soaps, paints, dyes,

varnishes, drugs and flavouring extracts.
2. It is a starting material used in the manufacture of many important compounds e.g.
ethanol, ethanoic acid, ethylester and ethoxyethane.
3. It is used as a fuel, either by itself or mixed with petrol in racing cars and rockets.
4. It is used as anti-freeze in automobile radiators because of its low freezing point -
117oC.
5. It is used for many alcoholic beverages such as beer, wine etc.
6. It is used as an antispectic in:
i. Surgical sport for hardening of skin.
ii. Sterilization such as cleaning skin before injection.
iii. Preservation of biological specimen and food.
7. It is used in ships compasses, spirit levels and in thermometer designed to measure
low temperatures.