A Levels Chemistry (9701)•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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