Arrange the following carbanions in the decreasing order of stability
[ADD IMAGE: Five para-substituted benzyl carbanion structures. I: p-Br-C6H4-CH2(-). II: C6H5-CH2(-) (plain benzyl carbanion). III: p-CH3O-C6H4-CH2(-). IV: p-CHO-C6H4-CH2(-). V: p-CH3-C6H4-CH2(-).]
Choose the correct answer from the options given below :
- A
I > II > IV > V > III
- B
I > IV > II > V > III
- C
IV > I > II > V > III
- D
IV > II > I > III > V
Carbanions are stabilised by electron-withdrawing groups (which delocalise the negative charge) and destabilised by electron-donating groups.
Ranking by substituent:
IV (, strong ): most stabilising → most stable
I (, effect dominant over weak ): mildly stabilising
II (, no effect): reference
V (, weak , ): mildly destabilising
III (, strong ): most destabilising → least stable
Order: IV > I > II > V > III.
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