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Which of the following benzyl cations is the most stable?

1. p-NO2-C6H4-CH2+
2. C6H5-CH2+
3. p-Cl-C6H4-CH2+
4. p-CH3O-C6H4-CH2+

Correct answer: p-CH3O-C6H4-CH2+

Solution

A benzylic cation is stabilized by electron-donating substituents and destabilized by electron-withdrawing ones. The para-methoxy group is a powerful pi-donor (+M), feeding electron density directly into the positive center, making p-CH3O-C6H4-CH2+ the most stable. NO2 and Cl are electron-withdrawing and destabilize it.

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