CHAPTER 15

HYDROXY COMPOUNDS
 LEARNING OUTCOMES

Give the general formula of alcohol.

Draw the structures, classify and name
the hydroxy compounds (C1 C10)
according to the IUPAC nomenclature
(include phenols).
Explain the physical properties:
boiling point
solubility
 Introduction:

The hydroxyl group (-OH) : functional

group

2 types of hydroxy compounds -

aliphatic alcohol & aromatic alcohol
(phenol)
Aliphatic alcohol
CnH2n+1OH
OH attached to alkyl group, R
IUPAC nomenclature
e (alkane) ol (alcohol)
eg :-
1. CH3CH2OH : ethanol
2. CH3CH2CH2OH : propanol
 Classification of alcohols:
1,2 & 3 alcohols
primary alcohol (1) OH group attached to
1 carbon (eg: CH3CH2OH - ethanol)

secondary alcohol (2) OH group attached

to 2 carbon (eg: 2-butanol)

tertiary alcohol (3) OH group attached to

3 carbon (2-methyl-2-propanol)
 Nomenclature of Alcohol
a) Aliphatic alcohol

i. The parent alcohol - the longest C

chain with OH group attached to it
OH group is given the lowest number
in the chain.
 OH

CH3CH2CHCH3 2- butanol

CH3 OH

CH3CCH2CHCH3

CH3 4,4-dimethyl-2-pentanol
 OH

CH3CH2CHCHCH3 3-pentanol

OH

cyclopentanol
ii. When there are two or more OH
groups present, the name ends
with diol, triol and so on.

OH OH

CH3CHCH2CHCH3 2,4-pentanediol

OH

CH3CCH2OH 1,2,2-propanetriol

OH
b) Aromatic alcohol (phenols)
In most cases, the name phenol is
used as the parents name.

OH OH

NO2
CH3

4-methylphenols 3-nitrophenols
(4-methyl hydroxybenzene)
 Physical Properties of Alcohol:
(i) Boiling point
The boiling point of an alcohol is always much higher than
that of the alkane with the same number of carbon atoms.
Intermolecular forces:
Between alkanes, the presence of van der Waals
forces.
Between alcohols, the presence of hydrogen
bonding
Hydrogen bonding are much stronger than VdW
forces and therefore it takes more energy to
separate alcohol molecules than it does to separate
alkane molecules.
Therefore, boiling point of alcohols is higher than
alkanes.
 H Boiling point of
R O alcohol is higher

H
because intermolecular
hydrogen bonds exits
between the OH
R O groups in the alcohol
molecules.
H
R O
 The boiling points of the alcohols increase
as the number of carbon atoms increases.
Alcohols with lower number of carbons
has smaller size compared to alcohols
with higher number of carbons.
Alcohols with smaller size will have
weaker van der Waals forces instead of
hydrogen bonding that is formed between
OH group.
Therefore, alcohols with lower number of
carbons have lower boiling points.
 The boiling points of the alcohol increase
as the number of OH group increase.
Alcohol which has more OH group means it
can form more H-bonds.
Example :
Boiling point of 1,3-butanediol > butanol

CH3CH(OH)CH2CH2OH > CH3CH2CH2CH2OH

 Straight chain alcohol has higher boiling
point than branched alcohol.
Straight chain alcohol Big surface area
strong VDW forces.
Thus, boiling points of 1 ROH > 2 ROH >
3 ROH
Example :
CH3CH2CH2CH2CH2OH ( 1 ROH ) >
CH3CH(OH)CH(CH3)CH3 ( 2 ROH ) >
CH3C(OH)(CH3)CH2CH3 ( 3 ROH )
(ii) Solubility

The lower alcohols (eg :- methanol,

ethanol, propanol and tert-butyl
alcohol) are completely miscible
with water.

Because of hydrogen bonding

between a water molecule and a
alcohol molecule.
 H O H
hydrogen bond
R OH
Alcohol contain polar end ( -OH group )
and a non-polar end ( alkyl group )
Polar end ( Hydrophilic ) soluble in water
Non polar end insoluble in water
( Hydrophobic )

Thus, as the alkane-like alkyl group

(hydrophobic @ water hating) becomes larger,
water solubility decrease.
 Exercise:
Give the structure of:
a) 3-ethyl-2-methyl-1-hexanol
b) 3-cyclohexyl-2-methyl-2-butanol
c) 3-methyl-3-hexanol
d) 4-methyl-3-phenyl-2-hexanol
e) 1-ethylcyclohexanol