Alcohols 2

CLASSES OF ALCOHOL
 Alcohols can be divided into three

classes: primary, secondary and teritiary
 Primary (1o) Alcohols have the carbon
with the OH group attached, joined to 1
or 0 other carbon atoms.
In the 1o alcohol
the carbon atom H H H Propan-1-ol
with the OH
group, will have 2 H C - C - C OH
hydrogen atoms
attached H H H
 Secondary (2o) Alcohol are those in
which the carbon attached to the OH
group is attached to two (2) other
carbon atoms
In the 2o alcohol
H OH H the carbon atom
with the OH
H C-C-C H group, will have 1
hydrogen atom
H H H
attached
Propan-2-ol
 Teritiary alcohols (3o)are those in
which the carbon attached to the OH
group is attached to three (3) other
carbon atoms
H OH H
H C-C-C H
In the 3o alcohol H H
the carbon atom H C H
with the OH
2-methyl propan-2-ol
group, will have H
no hydrogen
atoms attached
Reactivity of Alcohols
 Alcohols are polar molecules
 The polarity lies in the C - O - H bonds
and not in the hydrocarbon chain
 Polarity is as a result of significant
difference in electronegativity of the
atoms involved in the bond.
 Electronegativity is
 The bond being strongly polar C+- O-- H+
is responsible for all alcohols being
susceptible to attack by charged species
 Species known as nucleophiles
(negatively charged) can attack C+
 O- will be susceptible to attack by
electrophiles (positively charged species)
 When the C - O - H bond is broken the
oxygen will receive both shared electrons
because it is so electronegative
Look at the alcohol below
H H H
H C-C-C O-H
H H H
 So if the if O-H bond breaks we will get

the ions:
C H O:-
and H+
3 7
The formation of a H+ (proton) suggest

that alcohols can be acidic
 If the C - O bond breaks we will get the
ions:
C H +
and OH-
3 7
 Hence we can say that in this situation

alcohols might react by loss of OH-
 This is what occurs in many reactions of
alcohols.
Reactions of Alcohols
 Reactions with
 Acidified potassium permanganate
 Acidified potassium dichromate
 Carboxylic acids (R-COOH)
 Conc. sulphuric acid (H2SO4)
I , NaOH: iodoform test
2
Oxidation of Alcohols
 When alcohols react with acidified
KMnO4 and K2Cr2O7 oxidation takes
place.
 KMnO4 will change from purple to clear
 K2Cr2O7 will change from orange to
green
 The products formed depend on the
class of alcohol being oxidized
 Primary alcohols are oxidized to
aldehydes and can be further oxidized
to carboxylic acids
For example: propan-1-ol and KMnO4
H H H H H
[O] O
H C - C - C OH H C-C-C
H H H H H H
Propanol Propanal(Aldehyde)
H H [O]
O
H C-C-C Propanoic
OH acid
H H
 Secondary alcohols are oxidized to
ketones, no further oxidation takes place
H H H H H
H C-C-C H H C-C-C H
H OH H H O H
Propan-2-ol Propanone
(ketone)
 Teritiary alcohols are not oxidized.
Strong oxidisers cause their molecules to
be broken up, giving a mixture of oxidation
products
 The oxidation of 1o, 2o, 3o alcohols can be
use to distinguish between them
 The inability of 3o alcohols to undergo
oxidation and the inability of the ketones to
be further oxidized is due no available
hydrogen on the carbon with the
functional or leaving group.
3o alcohol Ketone produced
H OH H from oxidation of 2o
alcohol
H C-C-C H
H H
H H
H C-C-C H
H C H
No available H O H
H hydrogen on
carbon with -OH
group No available
hydrogen on
carbon with
functional group
 During oxidation it is the hydrogen that is
removed (removal of hydrogen is
oxidation)
 The carbon atom with the OH group in 3o
alcohols has no hydrogen attached to be
oxidized, hence reason for not being able
to undergo oxidation.
 The carbon atom (with the functional group)
in the ketone that is produced from the 2o
alcohol has no more hydrogen available
for further oxidation.
Reaction with Conc. H2SO4
 Alcohols react with concentrated
sulphuric acid at 180o to produce
alkenes
 The reaction is called a dehydration
reaction because a molecule of water is
removed
 Also at the end of the reaction sulphuric
acid is regenerated and can be thought
of as acting as a catalyst in the reaction
 For example: Ethanol and Sulphuric acid
H H H H H H
180o
H C - C - C H + H2SO4 H C-C=C H
H H OH H
+ H2O
Reaction with Carboxylic Acid
 Alcohols react with carboxylic acid to
produce a sweet smelling compound
called esters
 A molecule of water is also eliminated in
the formation of the ester.
 The reaction is catalyzed by a strong
acid such as sulphuric acid
 The reaction does not go to completion
 General Reaction
O O
+ H+
R-C - OH H -O -R R - C - O - R1
Acid Alcohol Ester
+ H2O
O O
+ H+
CH3 - C -OH H -O - CH3 CH3 - C - O-CH3
Ethanoic Methanol Methyl ethanoate
acid
+ H2O
Iodoform reaction
 The iodoform reaction is the reaction
of an alcohol with iodine and sodium
hydroxide.
 The alcohol must be of the form
OH
CH3 - CH - R
 Therefore it will not work with methanol
or propan-1-ol
 Using the general formula: CH3COR
R can be a hydrogen as in an alcohol or
aldehyde
 OrR can be an alkyl group as in
secondary alcohols or ketones
 The reaction is carried out by warming
the alcohol with a solution of iodine and
sodium hydroxide.
 Alcohols with the form given will form a
yellow precipitate of triiodomethane
 For example:
OH
CH3 - CH - R + 4I2 + 6NaOH
I O
H C-I + R - C ONa + 5NaI + 5H2O
I
Triiodomethane
(yellow precipitate)

Alcohols 2

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CLASSES OF ALCOHOL

 Alcohols can be divided into three

 So if the if O-H bond breaks we will get

The formation of a H+ (proton) suggest

 Hence we can say that in this situation

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