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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc107

Cyclopentadiene reacts with maleic anhydride at room temperature. Which of the following statements are correct? Select all that apply.

  1. AThe endo adduct is chiral and is formed as a racemate
  2. BThe endo adduct is the kinetically favoured major product
  3. CThe reaction is a concerted [4+2] cycloaddition in which both new bonds form on the same face of each component
  4. DThe two carbonyl groups of the anhydride end up cis to each other, fixed by the geometry of the dienophile

Answer: B, C, D

The Diels-Alder reaction is concerted and suprafacial, so the cis geometry of maleic anhydride is retained, and secondary orbital overlap favours the endo adduct (the endo rule). The bicyclic endo adduct has a mirror plane through the bridge carbon and the anhydride oxygen, so it is achiral (meso-like). The statement that it is chiral and racemic is incorrect.
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