MolSynapsequestion bank
MolSynapse / Question bank / Hydrocarbons / Conjugated dienes and Diels-Alder reaction
JEE Advanced levelSingle correct optionDifficulty 3 of 3hc109

Cyclohexa-1,3-diene reacts with one equivalent of HBr. The 1,2-adduct and the 1,4-adduct are best described as

  1. A4-bromocyclohexene and 3-bromocyclohexene respectively
  2. Bthe same constitutional compound, 3-bromocyclohexene
  3. C3-bromocyclohexene and 4-bromocyclohexene respectively
  4. D3-bromocyclohexene and 1-bromocyclohexene respectively

Answer: B

Protonation at C-1 gives the allylic cation over C-2, C-3 and C-4. Bromide at C-2 (1,2-addition) gives a bromide on the carbon next to a C=C between C-3 and C-4. Bromide at C-4 (1,4-addition) gives a bromide on the carbon next to a C=C between C-2 and C-3. Both are 3-bromocyclohexene, enantiomers of each other, so the 1,2/1,4 distinction does not give different constitutions here.
Practice Hydrocarbons More on Conjugated dienes and Diels-Alder reaction

More questions on Conjugated dienes and Diels-Alder reaction