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REACTION OF THE DAY_04

Chemistry

Benzoin Condensation

The Benzoin Condensation is a coupling reaction between two aldehydes that allows the preparation of
α-hydroxyketones. This method is only suitable for aromatic aldehydes.
Mechanism of Benzoin Condensation
Addition of the cyanide ion to create a cyanohydrin.

A strong base is now able to deprotonate at the former carbonyl C-atom:

A second equivalent of aldehyde reacts with this carbanion.

(1)
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Try Yourself
1. Consider the following reaction

KCN  alc.
Ph – CHO  Major Product P 


The degree of unsaturation of P is

(1) 8 (2) 9
(3) 10 (4) 7
2. Consider the following reaction

CHO

(X) + –CN

Me

The attack of –CN on X should be called as

(1) Nucleophilic substitution reaction (2) Electrophilic addition reaction
(3) Nucleophilic addition reaction (4) Acid base reaction
3. Consider the following reaction

O
KCN alc. PCC
Ph – C – H  

 P   Q

Identify the correct statement

(1) P has 2 chiral centres
(2) Two geometrical isomer are possible for Q
(3) Tautomerism is not possible in Q
(4) Conversion of P to Q is reduction

(2)
4. Consider the following reaction

CH
KCN alc.
  Product (P)

CH 3

P is

O O

(1) (2)
OH

OH OH

(3) (4)
O
O

5. Consider the following reaction

CHO CHO

Na2CO3 KCN
A B C

CHO

Product ‘C’ is

(1)
O

O
OH

(2) OH
O

OH
O
(3) O
O

O
O
(4) O
OH

(3)
Answer of Question Based on Beckmann Rearrangement
1. Answer (1)
2. Answer (1)
3. Answer (3)
4. Answer (1)
5. Answer (1)

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