Question

Formation of alcohol by oxymercuration- demercuration of alkenes

• A. involves carbocations and rearrangement
• B. involves carbanions and retoangement
• C. is stereospecific
• D. does not involve rearrangement and carbocation

Answer 1

Answer: (D)

Oxymercuration-demercuration of alkenes involves following steps :
(i) Dissociation of mercury (II) acetate
$C{H}_{3}COO-Hg-OCOC{H}_3⟶\underset{\text{electrophile}}{C{H}_{3}COO-H{g}^{+}}+C{H}_{3}CO{O}^{-}$
(ii) Attack of electrophile on double bond of alkene

(iii) Addition of water

Hence, oxymercuration-demercuration process involves, reduction and bridged mercurinium ion formation.