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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc106

For the addition of HBr to buta-1,3-diene, which of the following statements are correct? Select all that apply.

  1. AThe 1,2- and 1,4-adducts arise from two different carbocation intermediates
  2. BThe 1,2-adduct can rearrange to the 1,4-adduct on warming through the same allylic cation
  3. CAt about the 1,4-adduct 1-bromobut-2-ene is the major product (thermodynamic control)
  4. DAt about the 1,2-adduct 3-bromobut-1-ene is the major product (kinetic control)

Answer: B, C, D

Both adducts come from one resonance-stabilised allylic cation, and , attacked by bromide at two positions. At low temperature the faster-forming 1,2-adduct dominates, and at higher temperature equilibration through the same cation gives the more stable 1,4-adduct. The last statement is therefore false.
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