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Heterolysis of which of the following compounds yields the most stable carbocation?

1. (CH3)3CBr
2. (C6H5)3CBr
3. (C6H5)2CHBr
4. C6H5CH2Br

Correct answer: (C6H5)3CBr

Solution

On heterolysis the C-Br bond breaks to give a carbocation. (C6H5)3CBr gives the triphenylmethyl (trityl) cation, stabilised by three phenyl rings through extensive resonance, making it the most stable among the choices.

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