Q23 / 180 · COMEDK 2023 (Morning Shift) · Chemistry
Product of the following reaction is
- A
- B
- C
- Correct answerD
Solution
The reaction is intramolecular oxymercuration-demercuration on $\alpha$-terpineol.
$Hg(OAc)_2$ activates the double bond forming a mercurinium ion intermediate. The $-OH$ group in the molecule acts as an internal nucleophile, attacking the more substituted (tertiary) carbon of the mercurinium ion (Markovnikov selectivity), forming a stable 6-membered cyclic ether ring bridging the cyclohexane ring.
$NaBH_4$ then reduces the C$-$Hg bond, replacing Hg with H.
The product is a bicyclic ether (1,8-cineole/eucalyptol) with oxygen bridging to the tertiary carbon — option (4).
$Hg(OAc)_2$ activates the double bond forming a mercurinium ion intermediate. The $-OH$ group in the molecule acts as an internal nucleophile, attacking the more substituted (tertiary) carbon of the mercurinium ion (Markovnikov selectivity), forming a stable 6-membered cyclic ether ring bridging the cyclohexane ring.
$NaBH_4$ then reduces the C$-$Hg bond, replacing Hg with H.
The product is a bicyclic ether (1,8-cineole/eucalyptol) with oxygen bridging to the tertiary carbon — option (4).
Hence, the correct answer is option: 'D'.