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JEE Advanced levelSingle correct optionDifficulty 3 of 3o4088

The second-order rate constant for alkene formation from with in ethanol at is . For under the same conditions it is . The best conclusion is

  1. A: the C-H bond is broken in the rate-determining step, together with loss of bromide in one concerted step (E2)
  2. B: ionisation of the C-Br bond is rate determining and a carbocation is formed (E1)
  3. C: the reaction is SN2 at the alpha carbon, with no involvement of the beta C-H bond
  4. D: no C-H bond cleavage occurs in the rate-determining step

Answer: A

The ratio is , a large primary kinetic isotope effect. A C-H bond (not C-Br alone) is therefore broken in the rate-determining step. With second-order kinetics and a secondary halide without acidic hydrogens, this is the concerted E2 mechanism. In E1 the isotope effect would be close to 1.
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