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The primary chloride shown undergoes solvolysis in aqueous acetone far faster than a simple primary alkyl chloride such as ethyl chloride. What is the main reason?

  1. AThe benzyl cation is stabilised by resonance with the ring
  2. BThe ring makes the carbon more hindered
  3. CThe C-Cl bond is shorter than in ethyl chloride
  4. DBenzyl chloride is a tertiary halide

Answer: A

The compound is benzyl chloride. Ionisation gives the benzyl cation, whose positive charge is delocalised into the aromatic ring over the ortho and para positions. This lowers the energy of the transition state, so it solvolyses much faster than ethyl chloride, whose cation has no such stabilisation.
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