Arrange the following carbanions in the decreasing order of stability. I. p-Br-C6H4- CH2 II. C6H5- CH2 III. p-CH3O-C6H4- CH2 IV. p-CHO-C6H4- CH2 V. p-CH3-C6H4- CH2 Choose the correct answer from the options given below :
- I > II > IV > V > III
- IV > II > I > III > V
- I > IV > II > V > III
- IV > I > II > V > III
Answer
(4) IV > I > II > V > III
Solution
A benzyl carbanion is stabilised by electron-withdrawing groups and destabilised by electron-donating groups at the para position.
IV: –CHO is a strong –R (–M) group; the negative charge is delocalised up to the carbonyl oxygen most stable.
I: –Br withdraws electrons by –I effect (–I > +R) more stable than unsubstituted II.
II: no substituent (reference).
V: –CH3 donates by +I and hyperconjugation less stable than II.
III: –OCH3 donates strongly by +R effect least stable.
IV > I > II > V > III
Answer: (4)