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Question
Arrange the following carbanions in order of their decreasing stability.
(A) H3C – C ≡ C–
(B) H – C ≡ C–
(C) \[\ce{H3C - C\overset{-}{H2}}\]
Options
A > B > C
B > A > C
C > B > A
C > A > B
Solution
B > A > C
Explanation:
The order of decreasing stability of carbanions is:
\[\ce{\underset{(B)}{H - C ≡ C-} > \underset{(A)}{CH3 - C ≡ C-} > \underset{(C)}{CH3 - CH-}}\]
sp-hybridised carbon atom is more electronegative than sp3-hybridised carbon atom and hence, can accommodate the negative charge more effectively. – CH3 group has +1 effect, therefore, it intensifies the negative charge and, hence, destabilises the carbanion CH3 →C = C–.
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