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JEE Main levelSingle correct optionDifficulty 2 of 3o4177

The reaction of 2-bromopropane and of its hexadeuterated analogue with in ethanol gives . This large primary kinetic isotope effect shows that:

  1. Aa carbocation is formed in the rate-determining step, as in E1
  2. Bthe rate-determining step is SN2 attack of ethoxide on carbon
  3. Cthe C-Br bond breaks first in a slow step and the C-H bond breaks in a later fast step
  4. Dthe C-H (C-D) bond is broken in the rate-determining step, as expected for an E2 mechanism

Answer: D

A well above 1 means a bond to the isotope is being broken in the slow step. That happens in E2, where C-H cleavage and C-Br cleavage occur together. In E1 the C-H bond breaks after the slow ionisation, so the isotope effect is close to 1.
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