medium · MCAT chem-phys

Allyl bromide (CH_2=CHCH_2Br) is exceptionally reactive in both S_N1 and S_N2 reactions.

What factor enhances its S_N1 reactivity?

  1. Bromine is more electronegative in the allylic position.
  2. Resonance stabilization of the resulting carbocation.
  3. The primary carbon is not sterically hindered.
  4. The double bond acts as a nucleophile.

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