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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3229

The primary allylic chloride shown (double bond geometry not specified) can react by either pathway. Select all correct statements.

  1. AIts reaction with in acetone is faster than that of 1-chlorobutane
  2. BHydrolysis by can give two constitutionally isomeric alcohols
  3. CIt cannot undergo because the carbon attached to Cl is part of a double bond
  4. DThe intermediate is an unstabilised primary carbocation

Answer: A, B

The compound is 1-chlorobut-2-ene (crotyl chloride). Its transition state is stabilised by overlap with the adjacent pi system, so it is faster than 1-chlorobutane. Its cation is the allyl cation , so water can attack at either end and give two constitutionally isomeric alcohols. The halogen is on an carbon, so is possible, and the cation is resonance stabilised, not an unstabilised primary one. Correct: the first two.
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