Date- 24-10-2020

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REACTION OF THE DAY

Chemistry

Aldol Reaction

'Aldol' is an abbreviation of aldehyde and alcohol.

Aldehydes and ketones having atleast one -Hydrogen atom take part in Aldol condensation in the presence of
dilute alkali or acid. Two molecules of carbonyl compound condense to form a -hydroxy aldehyde or -hydroxy
ketone which gets dehydrated on heating into ,-unsaturated aldehyde or ketone.
Acidity of -H atoms of carbonyl compounds is due to strong e– withdrawing effect of carbonyl group and
resonance stabilisation of the conjugate base.
–
O O O
–
C C C C C C
–
H B

Mechanism of the Aldol Addition

Base Catalyzed:

(1)
Acid Catalyzed :

Aldol Condensation
In some cases, the adducts obtained from the Aldol Addition can easily be converted to , -unsatur-
ated carbonyl compounds. The formation of the conjugated system is the driving force for this spon-
taneous dehydration.

Mechanism of the Aldol Condensation

Acid Catalyzed condensation :

Base catalyzed condensation :

Cross Aldol Condensation: When Aldol condensation is carried out between two different aldehydes and/or
ketones, it is called cross Aldol condensation. If both the molecules have -H atom, then they can give a mixture
of four-condensation products.

(i) NaOH
Ex. CH3 CHO  CH3 CH2CHO 
(ii) 

Four possible products are formed as following :

(2)
 (i) NaOH
2CH3 CHO 
(ii) 
CH3 CH  CH  CHO (Self aldol product)
But-2-enal

(i) NaOH
2CH3 CH2CHO 
(ii) 
CH3 CH2CH  C — CHO (Self aldol product)
|
CH3
2-Methylpent-2-enal

(i) NaOH
CH3 CHO  H.CHCHO 
(ii) 
CH3CH  C — CHO (Cross aldol product)
| |
CH3 CH3
2-Methylbut-2-enal

(i) NaOH
CH3 — CH2CHO  CH3CHO 
(ii) 
CH3CH2CH  CH — CHO (Cross aldol product)
Pent-2-enal

Hence cross aldol condensation becomes useful when one of the carbonyl compound does not contain -
H atom.

OH
|
dil. NaOH 
Ex. HCHO  CH3 CHO   CH2 — CH2CHO  CH2  CH — CHO
H O 2



Try Yourself
1. What is the major product in following reaction?
O O
dil. NaOH
CH3 C (CH2)3 C H

CH3
CH3
C O
C O
(1) (2)

CH3
O C O

(3) (4)

CH3

Answer of Question Based on Wurtz Reaction

1. Answer (1)

(3)