Draw the structures of alkenes that would yield the...

Draw the structures of alkenes that would yield the following alcohols on hydration (red $=\mathrm{O}$ ). Tell in each case whether you would use hydroboration-oxidation or oxymercuration-demercuration.

Key Concepts

Alkene Hydration

Alkene hydration is the transformation in which water is added across a carbon–carbon double bond to form an alcohol. This reaction is fundamental in organic synthesis and can proceed via different reaction pathways, each with its own regioselectivity and mechanism of action.

Markovnikov and Anti-Markovnikov Regiochemistry

Markovnikov's rule describes the regioselective outcome in many additions to alkenes, where the hydrogen atom adds to the less substituted carbon of the double bond, leading to the more substituted alcohol. Conversely, anti-Markovnikov addition refers to cases where the regioselectivity is inverted, for example, when using hydroboration-oxidation, which delivers the hydroxyl group to the less substituted carbon.

Hydroboration-Oxidation

Hydroboration-oxidation is a two-step process involving the syn addition of a boron reagent to an alkene followed by oxidation. This method results in anti-Markovnikov addition of water, avoids carbocation intermediates, and is valued for its stereospecificity and mild reaction conditions.

Oxymercuration-Demercuration

Oxymercuration-demercuration is a two-step sequence that hydrates alkenes via formation of a mercurinium ion intermediate, which leads to Markovnikov addition of water. This method prevents carbocation rearrangements and offers a controlled way to hydrate alkenes under relatively mild conditions.

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