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JEE Main levelSingle correct optionDifficulty 2 of 3hc192

Buta-1,3-diene reacts with dimethyl fumarate (dimethyl (E)-but-2-enedioate) in a Diels-Alder reaction. The product is:

AMeso cis-dimethyl cyclohex-4-ene-1,2-dicarboxylate
BRacemic trans-dimethyl cyclohex-4-ene-1,2-dicarboxylate
CA single enantiomer of the trans diester
DMeso trans-dimethyl cyclohex-4-ene-1,2-dicarboxylate

Answer: B

The reaction is stereospecific: the trans arrangement of the ester groups in the E-dienophile is retained. The trans-1,2-disubstituted cyclohexene is chiral, and attack on either face of the planar alkene gives both enantiomers equally, so the product is racemic.

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