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Reaction of trans-2-phenyl-1-bromocyclopentane with alcoholic produces:

  1. A
    4-phenylcyclopentene
  2. B
    2-phenylcyclopentene
  3. C
    1-phenylcyclopentene
  4. D
    3-phenylcyclopentene

Solution & Step-by-step Explanation

This is an elimination reaction. reactions require an anti-periplanar orientation of the Leaving Group (Br) and the beta-hydrogen.In trans-2-phenyl-1-bromocyclopentane, the Br and the Phenyl group are on opposite sides. This means the Hydrogen on C-2 (where Phenyl is) is cis to the Bromine.Therefore, the elimination cannot happen using the hydrogen on C-2. It must use the hydrogen on C-5.Elimination between C-1 and C-5 gives 3-phenylcyclopentene.

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Try it yourself before checking the explanation above.

Reaction of trans-2-phenyl-1-bromocyclopentane with alcoholic produces:
A
4-phenylcyclopentene
B
2-phenylcyclopentene
C
1-phenylcyclopentene
D
3-phenylcyclopentene

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