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Question

Find out the order of stability between (A) CH3−CH2−C|COOHH−−CH−CH3
(B) CH3−C|COOHH−CH2−−CH−CH3
(C) C|COOHH2−CH2−CH2−−CH−CH3

A
A>B>C
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B
B>A>C
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C
C>A>B
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D
B>C>A
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Solution

The correct option is A A>B>C
COOH is an electron withdrawing group. Therefore, it will increase the stability of the carbanion by withdrawing electron and decreasing electron density on carbanion.
As the distance between the electron withdrawing group (COOH) and carbanion carbon increases,the -I effect of (COOH) group decreases as -I effect is distance dependent and vanishes after 2nd carbon.
Therefore, the order of stability of carbanion is:
A>B>C

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