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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3155

Assertion (A): Free radical bromination of alkanes is much more selective than chlorination. Reason (R): The hydrogen abstraction by is endothermic, so its transition state is late and resembles the alkyl radical.

  1. ABoth A and R are true but R is not the correct explanation of A.
  2. BA is true but R is false.
  3. CA is false but R is true.
  4. DBoth A and R are true and R is the correct explanation of A.

Answer: D

Bromination is indeed far more selective (tertiary : primary of about 1600 : 1 against about 5 : 1 for chlorination). Abstraction by is endothermic, so by the Hammond postulate the transition state is late and carries much radical character. The difference in radical stability is then felt strongly, and R correctly explains A.
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