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10 Gabriel Synthesis

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Mayank Chauhan
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43 views

10 Gabriel Synthesis

Uploaded by

Mayank Chauhan
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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REACTION OF THE DAY_10


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
1. Which of the following compounds can be prepared in good yield by Gabriel phthalimide synthesis?
NH 2 O

CH 2 – C – NH2
(1) (2)

CH 2NH 2

(3) (4) CH3 – CH2 – NHCH3

2. The major product of the following reaction is

O
C
(i) KOH
NH
C (ii) Br CH2 Cl
O

O O
C C
(1) N–CH2 Br (2) N CH2Cl
C C
O O

(2)
O O
C C
(3) N (4) N

O–CH2– Br O CH2Cl

3. Which of the following is the best method to produce 1° aliphatic amine?


(1) Hydrogenation of R – NC (2) Reaction of alkylhalides with NH3
(3) Gabriel phthalimide synthesis (4) Hydrolysis of amides
4. Consider the following reaction

KMnO4/  NH 3 KOH(aq) (i). HO – (CH 2)2 – Br


P Q R S
 (ii). H +, 
The product ‘S’ may contain

COOH
(1) + HO – CH2 – CH2 – NH2 + KBr
COOH
COOH
(2) + HO – CH2 – CH2 – NH2 + KBr
COOH

COOH
(3) + + NH3 + KBr
COOH O

COOH
+ + NH3 + KBr
(4)
O
COOH

O
*
1. KOH (aq.) Br COOEt
NH I major product
5.

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

(3)
Answer of Question Based on Friedel-Crafts Acylation & Alkylation
1. Answer (2)
2. Answer (2).
3. Answer (1)
4. Answer (2)
5. Answer (1)



(4)

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