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Gabriel Synthesis: Reaction of The Day

The document discusses the Gabriel synthesis, which allows the preparation of primary amines from alkyl halides. It involves reacting potassium phthalimide with an alkyl halide, which results in alkylation. The product is then cleaved by reaction with a base or hydrazine, yielding a stable cyclic product. It provides an example reaction and asks which is the major product when potassium phthalimide reacts with bromoethyl acetate. The answer is given as option 1, which depicts the primary amine product after cleavage.

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68 views2 pages

Gabriel Synthesis: Reaction of The Day

The document discusses the Gabriel synthesis, which allows the preparation of primary amines from alkyl halides. It involves reacting potassium phthalimide with an alkyl halide, which results in alkylation. The product is then cleaved by reaction with a base or hydrazine, yielding a stable cyclic product. It provides an example reaction and asks which is the major product when potassium phthalimide reacts with bromoethyl acetate. The answer is given as option 1, which depicts the primary amine product after cleavage.

Uploaded by

vishesh
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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Date- 09-12-2020

Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Ph.: 011-47623456

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)

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