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A Levels Chemistry (9701)•9701/12/M/J/22
Question 32 from 9701/12/M/J/22

Explanation

Vicinal dibromide cyclizes with ammonia to form 2-substituted aziridine Steps:

  • Analyze coniine's structure as a 2-alkylaziridine formed via double SN2 by NH3 on vicinal dibromide.
  • The dibromide's CH2Br becomes one aziridine CH2; the CHBr-R becomes the substituted CH-R.
  • Match R to coniine's alkyl substituent: ethyl requires -CH2CH3 on the second carbon.
  • Select the dibromide with four-carbon chain ending in ethyl: BrCH2-CHBr-CH2CH3.

Why D is correct:

  • BrCH2CHBrCH2CH3 cyclizes to 2-ethylaziridine, matching coniine's formula and structure via ring closure.

Why the others are wrong:

  • A: Cyclopentane ring creates bicyclic product, not simple aziridine.
  • B: Propyl and cyclopentane yield complex fused ring, mismatched skeleton.
  • C: Forms 2-methylaziridine (from -CH3), wrong alkyl chain length.

Final answer: D

Topic: Organic synthesis

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