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Question: Answered & Verified by Expert
2-Phenylethylbromide when heated with $\mathrm{NaOEt}$, elimination takes place. No deuterium exchange takes place when the reaction is carried out in $\mathrm{C}_2 \mathrm{H}_5 \mathrm{OD}$ solvent. The mechanism will be
ChemistryHaloalkanes and HaloarenesAIIMSAIIMS 2009
Options:
  • A E1 elimination
  • B E2 elimination
  • C E1cB elimination
  • D $\mathrm{E} 2$ or E1cB.
Solution:
1290 Upvotes Verified Answer
The correct answer is: E2 elimination


It is a primary bromide. So it will undergo elimination either by E2 or E1cB. Since there is no deuterium exchange in $\mathrm{C}_2 \mathrm{H}_5 \mathrm{OD}$ solvent, $\mathrm{C}-\mathrm{H}$ bond is not broken to form carbanion. Hence the actual mechanism is E2 only.

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