Chapter 111 of 2363 min read

Reaction intermediates and types of reactions

Why this is asked: Carbocation stability (3° > 2° > 1° > methyl, from hyperconjugation and +I) is exactly reversed for carbanions (methyl > 1° > 2° > 3°) — alkyl groups that stabilise a positive centre by donating electron density destabilise a centre that's already electron-rich. Mixing up which intermediate benefits from alkyl substitution is the trap.

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Test yourself

•Among the given compounds I–III (shown), the correct order of bond dissociation energy of the C–H bond marked with * is:
•The most stable carbocation among the four structures shown is:

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