Cyclohexene on ozonolysis followed by reaction with zinc dust and water gives compound E. Compound E on further treatment with aqueous KOH yields compound F. Compound F is
(A)(see structure)✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)
Answer: (A)
Solution
Cyclohexene undergoes ozonolysis to form an ozonide, which on reductive workup with Zn/H₂O gives the dialdehyde OHC-(CH₂)₄-CHO (compound E). This dialdehyde undergoes intramolecular aldol condensation in aqueous KOH. One aldehyde acts as nucleophile (enolate) and attacks the other aldehyde carbonically, followed by dehydration, forming a cyclic product. The final product F is adipic acid HOOC-(CH₂)₄-COOH, formed by oxidation of the aldehyde groups under the basic conditions.
JEE Advanced · 2007 · 08 Apr 2007 · Paper 2 · Single correct option
