Date-30-04-2021

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REACTION OF THE DAY_05

Chemistry
Birch Reduction
Alkynes on reduction with sodium and liquid ammonia yields trans alkenes.

R H
Na/liq. NH3
R C C R C C
H R
trans-alkene

CH3 H
Na/liq. NH3
CH3 C C CH2 CH3 C C
H CH2 CH3
trans-pent-2-ene

This reaction is also known as Birch reduction

Mechanism of the Birch Reduction

The question of why the 1,3-diene is not formed, even though it would be more stable through conjugation, can
be rationalized with a simple mnemonic. When viewed in valence bond terms, electron-electron repulsions in the
radical anion will preferentially have the nonbonding electrons separated as much as possible, in a 1,4-relationship.
Reactions of arenes with +I- and +M-substituents lead to the products with the most highly substituted double
bonds:

(1)
 The effect of electron-withdrawing substituents on the Birch Reduction varies. For example, the reaction of benzoic
acid leads to 2,5-cyclohexadienecarboxylic acid, which can be rationalized on the basis of the carboxylic acid
stabilizing an adjacent anion:



Try Yourself
1. Complete the following reactions
OCH 3

Na,NH liq.
3
 

EtOH

OCH 3 OCH 3

(1) (2)

OCH 3 O

(3) (4)

2. Complete the following reactions

CH 3
Na/NH
  3

EtOH, Et 2O
HOOC
CH 3 CH 3

(1) (2)

COOH COOH

(2)
 CH 3
CH 3

(3) (4)

COOH
3. Complete the following reactions
COOH

1Li,liq. NH ,THF
3
   

2CH3I

CH3
H 3C CH 3 H 3C COOH

(1) (2)

COOH CH 3

HOOC CH 3 CH 3

(3) (4)

CH 3 CH 3
4. Complete the following reactions

Na/NH 3 H O+
 x 
   3 y
EtOH,Et 2O
N
The product y is

(1) (2)
O NH O
O

(3) (4)
O O O

OMe

1. Na, Liq NH3

5. N Br
major product
2.
O
O OMe
OMe

(3)
 OMe OMe

N N
O O
CH2 O OMe CH2 OMe
(1) (2) O

OMe
OMe

CH2 OMe CH2 OMe OMe

N N
(3) O (4) O
OMe
O O



Answer of Question Based on Benzoin Condensation

1. Answer (2)
2. Answer (3)
3. Answer (3)
4. Answer (2)
5. Answer (2)



(4)