Reaction of cyclohexene with mercury(II) acetate in CH3 OH rather than H2 O followed by treatmen

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Reaction of cyclohexene with mercury(II) acetate in CH3 OH...

Reaction of cyclohexene with mercury(II) acetate in $\mathrm{CH}_{3} \mathrm{OH}$ rather than $\mathrm{H}_{2} \mathrm{O}$ followed by treatment with $\mathrm{NaBH}_{4},$ yields cyclohexyl methyl ether rather than cyclohexanol. Suggest a mechanism.

Key Concepts

Regioselectivity of Nucleophilic Attack

In the oxymercuration mechanism, the nucleophilic attack on the cyclic mercurinium ion occurs in a regioselective manner, typically at the more substituted carbon atom. This preference is due to the stabilization of positive charge that develops during the transition state, dictating the final regioselectivity of the addition product.

Solvent as Nucleophile

The selection of the nucleophile in oxymercuration reactions is dictated by the solvent used. When methanol is the solvent, it acts as the nucleophile, attacking the mercurinium ion to yield a methoxy-substituted intermediate rather than a hydroxyl group. This results in the formation of an ether post-demercuration, contrasting with the formation of alcohols when water is the nucleophile.

Mercurinium Ion Intermediate

This intermediate is formed when mercury(II) acetate reacts with an alkene. The formation of a three-membered ring structure (the mercurinium ion) activates the alkene toward nucleophilic attack by providing a positively polarized system that is more susceptible to attack. The intermediate plays a crucial role in determining the regiochemistry of the nucleophilic addition in oxymercuration reactions.

Oxymercuration-Demercuration

This is a two-step reaction where mercury(II) acetate first reacts with an alkene to form a cyclic mercurinium ion intermediate, followed by nucleophilic attack by a solvent or water, leading to the formation of an organomercury intermediate. The subsequent demercuration step, commonly using NaBH?, replaces the mercury moiety with a hydrogen atom, completing the process. This mechanism avoids carbocation rearrangements often encountered in acid-catalyzed hydration reactions.

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