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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3050

Which of the following halides are practically unreactive towards SN1 solvolysis in aqueous ethanol?

  1. Abromobenzene
  2. Bbromoethene
  3. C1-bromobicyclo[2.2.1]heptane
  4. D1-bromo-1-methylcyclopentane

Answer: A, B, C

Bromobenzene and bromoethene would have to form aryl and vinyl cations, which are very unstable. The bridgehead bromide cannot form the planar cation in its rigid bicyclic skeleton. 1-Bromo-1-methylcyclopentane is an ordinary tertiary halide and solvolyses readily.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN1 vs SN2: substrate, nucleophile, solvent, leaving group

More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group