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A Levels Chemistry (9701)•9701/12/M/J/22
Question 31 from 9701/12/M/J/22

Explanation

Haloalkane structure determines hydrolysis mechanism

Steps:

  • Examine structures: P is tertiary haloalkane (three alkyl groups on carbon with halogen); Q is primary (one alkyl group).
  • Recall SN1 mechanism favored for tertiary halides due to stable carbocation formation; SN2 for primary due to backside attack without carbocation.
  • Hydrolysis of P proceeds via SN1 as rate depends only on alkyl halide concentration.
  • Hydrolysis of Q proceeds via SN2 as rate depends on both alkyl halide and nucleophile concentrations.

Why A is correct:

  • P is tertiary, so undergoes SN1 hydrolysis per the rule that 3° halides form stable 3° carbocations, accelerating unimolecular rate-determining step.

Why the others are wrong:

  • B: P (tertiary) cannot undergo SN2; steric hindrance blocks backside attack.
  • C: Q (primary) favors SN2, not SN1; primary carbocation is unstable.
  • D: Q undergoes SN2, but A correctly identifies P's mechanism; question seeks the specified correct row.

Final answer: A

Topic: Halogen compounds

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