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JEE Main levelSingle correct optionDifficulty 2 of 3g3134

In the hydrolysis of the rate-determining step is ionisation. The transition state of this step is best described as

  1. Asymmetrical, with the C-Br bond fully intact
  2. Bclose to the product alcohol
  3. Cclose to in structure, because the step is exothermic
  4. Dclose to the carbocation (ion pair) in structure, because the step is strongly endothermic

Answer: D

Formation of and from the neutral halide is endothermic. By the Hammond postulate the transition state is late and resembles the carbocation ion pair. For this reason features that stabilise the cation, such as extra alkyl groups, also lower the barrier.
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