Date- 09-12-2020

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REACTION OF THE DAY

Chemistry
Gabriel Synthesis

KOH, 
HO
O2

Potassium phthalimide allows the preparation of primary amines by reaction with alkyl halides.
After alkylation, the product is cleaved by reaction with base or hydrazine, which leads to a
stable cyclic product.
Mechanism of the Gabriel Synthesis

Note : Phthalimide is acidic

(1)
Cleavage:

Try Yourself
O
*
1. KOH (aq.) Br COOEt
NH I major product
1.

O
The major product of the above reaction is

O O
COOEt O
N *
N C CH Br
(1) * (2)
2

O O

O O
* O
COOEt
N N C CH2 Br
(3) (4) *

O O

Answer of Question Based on Fries Rearrangment

1. Answer (1)

(2)