MolSynapsequestion bank
MolSynapse / Question bank / Hydrocarbons / Alkyne hydration, hydroboration and Diels-Alder products
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc258

The dienophile shown reacts with buta-1,3-diene in a Diels-Alder reaction. Which statements about the adduct are correct?

  1. AThe adduct has two stereocentres.
  2. BThe adduct is a meso (achiral) compound.
  3. CThe adduct is formed as a racemic pair of enantiomers.
  4. DThe two ester groups are cis to each other on the new ring.

Answer: A, B, D

The compound shown is dimethyl maleate (Z). The reaction is stereospecific, so the cis esters end up cis on the cyclohexene ring, giving dimethyl cis-cyclohex-4-ene-1,2-dicarboxylate. This molecule has two stereocentres related by a mirror plane, so it is meso and achiral. A racemic pair would arise only from dimethyl fumarate (trans).
Practice Hydrocarbons More on Alkyne hydration, hydroboration and Diels-Alder products

More questions on Alkyne hydration, hydroboration and Diels-Alder products