PREPARATION OF

ALDEHYDES AND
KETONES

VIDEO 1
Objective
 Explain the preparation of carbonyl compounds
through these reactions:
a)Oxidation of alcohols
b)Ozonolysis of alkenes
c) Friedel–Crafts acylation to produce aromatic
ketones
1. OXIDATION OF ALCOHOLS

 Oxidation of primary alcohols to aldehyde

using pyridinium chlorochromate (PCC) in
anhydrous media such as dichloromethane.

 Secondry alcohols are oxidised to ketones

using oxidation agent such as PCC, chromic
acid or potassium dichromate and sulfuric
acid.
•

Example.

H O
l ll
PCC
CH3-C-OH CH3-C-H
CH2Cl2
l
H

ethanol ethanal
(alcohol 1°) (aldehyde)

VIDEO 2
 CH3 CH3
l KMnO4 l
CH3-C-OH CH3-C=O
l
H

2-propanol propanone

(alcohol 2°) (ketone)

 CH3
l
CH3-C-OH No reaction
l
CH3

2-methyl-2-propanol

(alcohol 3°)
2. OZONOLYSIS OF ALKENES

 The oxidative cleavage of a double bond

produced carbonyl-containing product.

 Hydrolysis of the ozonide intermediate in

the presence of zinc (reductive workup)
permits aldehyde products to be insolated
without further oxidation.

VIDEO 3
•

R’ R
l l O O
i) O3
C=C ll ll
l l ii) H2O/Zn R’CH + RCH
H H

R’ R O O
l l i) O3 ll ll
C=C
l l ii) H2O/Zn R’CR’’ + RCR’’’
R’’ R’’’
 EXAMPLE

CH3CH=CHCH2CH3 i) O3
ii) H2O/Zn
2-pentene

CH3CHO + CH3CH2CHO

ethanal propanal
 CH2CH3
l i) O3
CH3C=CHCH2CH3 ii) H2O/Zn

3-methyl-2-hexene
CH2CH3 O
l ll
CH3C=O + CH3CH2CH

2-butanone propanal
 i) O3
CH3
ii) H2O/Zn

4-methylcyclopentene
O O
ll ll
HCCH2CHCH2CH
l
CH3

3-methylpentandial
 3. FRIEDEL-CRAFTS
ACYLATION
 Acyl chloride or carboxylic acid anhydride
acylate aromatic ring in the presence of
aluminium chloride.
 The reaction is an electrophilic aromatic
substitution in which acylium ion
generated attack the ring.
 O O
+ R-C-Cl + AlCl3 -C-R

O O O
+ R-C-O-C-R + AlCl3 -C-R
 EXAMPLE
O
O ll
ll AlCl3 C-CH3
+
CH3CCl
Practice Questions

(a) CH3CH(Br)CH(CH3)OH + K2Cr2O7/H2SO4

(i) O3
(b) CH3CH=CCH(CH3)2
(ii)H2O/Zn
CH3

AlCl3
(c) + -C=O
Cl