MolSynapsequestion bank
MolSynapse / Question bank / Hydrocarbons / Conjugated dienes and Diels-Alder reaction
JEE Advanced levelSingle correct optionDifficulty 3 of 3hc103

2,3-Dimethylbuta-1,3-diene reacts with propenal () in a Diels-Alder reaction. The product is

  1. A3,4-dimethylcyclohex-3-ene-1-carbaldehyde
  2. B4,5-dimethylcyclohex-3-ene-1-carbaldehyde
  3. C2,3-dimethylcyclohex-3-ene-1-carbaldehyde
  4. D3,4-dimethylcyclohex-1-ene-1-carbaldehyde

Answer: A

The four diene carbons and the two dienophile carbons form a cyclohexene ring, the new C=C lying between the two methyl-bearing carbons. The CHO carbon is C-1 of the ring and the double bond must not involve C-1, so the lowest locants are 3,4 for both methyl groups and the double bond. The product is 3,4-dimethylcyclohex-3-ene-1-carbaldehyde.
Practice Hydrocarbons More on Conjugated dienes and Diels-Alder reaction

More questions on Conjugated dienes and Diels-Alder reaction