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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc197

(2E,4Z)-Hexa-2,4-diene reacts with ethene in a Diels-Alder reaction (assume it reacts). The product, 3,6-dimethylcyclohexene, is:

  1. AThe cis isomer, meso
  2. BThe trans isomer, formed as a racemic mixture
  3. CThe trans isomer, meso
  4. DThe cis isomer, racemic

Answer: B

In the diene, one terminal methyl is on the outside and one on the inside of the s-cis form, so after cycloaddition the two methyl groups end up on opposite faces of the ring (trans). The trans isomer is or , chiral and formed as a racemate. The cis isomer would be meso and would come from the (E,E) diene.
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