CI 13.

4 The –OH Group

The –OH group is one of the more common functional groups in organic
chemistry. It can be found in:
H H R’
 Alcohols: R-OH R-C-OH R-C-R’ R-C-R’’
H OH OH
1ry 2ry 3ry

 Phenols: PhOH [Ph = Phenyl = C6H5]

OH
Carboxylic Acids: RCOOH RCO2H
O


R-C
OH
Acidic Properties of alcohol can be compared to
water:

R-OH +H2O R-O- + H3O+ v H2O +H2O H-O- + H3O+

Acid strength:

O
CH3CH2OH < H2O < OH < R-C
OH
NO reaction Reacts with Reacts with strong base
with strong strong base to to give salt + water!!
bases or give salt + Reacts with carbonates
carbonates water!! to give CO2!

Stability of R-O- ion

determines acid strength i.e where equilibrium position lies. The
phenoxide and carboxylate anions are stabilised by the delocalisation of
the negative charge i.e
-
- O
O R-C
O
Oxidation of the OH Group:
The OH group can be oxidised using a strong oxidising agent such as
acidified dichromate solutions (Cr2O72-(aq)) .
However, there must be a hydrogen on the carbon to which the –OH
group is bonded. Therefore only 1ry and 2ry alcohols can be oxidised.
3ry alcohols, phenols and carboxylic acids cannot be oxidised

1ry alcohols aldehydes carboxylic acids

H
R-C-OH O O
H R-C R-C
Can be H OH
extracted if
careful

2ry alcohols ketones

H O
R-C-R’ R-C-R’
OH

Dehydration of alcohols:
Many alcohols (but not PhOH or RCOOH) can lose H2O to form an alkene
e.g OH + H2O

This is an example of an elimination reaction

FeCl3 Test: enols [C=C-OH] form purple complexes with FeCl3.

Esters: R-OH + R’COOH RCOOR’ [an ester] + H2O

O O
OH + + H2O
HO O
Aspirin [2-ethanoylhydroxybenzoic acid] is an example of an ester!