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12 MECHANISMS

Alcohols & Thiols

Alcohol via SN2

Alcohol via SN2

Hydroxide displaces a leaving group to give an alcohol.

Alcohol via SN1

Alcohol via SN1

A carbocation is trapped by water.

Alcohol via Alkene Hydration

Alcohol via Alkene Hydration

Acid-catalyzed Markovnikov hydration of an alkene.

Alcohol via Hydroboration

Alcohol via Hydroboration

Anti-Markovnikov alcohol from an alkene.

Hydride Reduction

Hydride Reduction

NaBH4 reduces a carbonyl to an alcohol.

Ester Reduction (LAH)

Ester Reduction (LAH)

LiAlH4 reduces an ester to a primary alcohol.

Grignard + Ketone

Grignard + Ketone

A Grignard reagent adds to give a tertiary alcohol.

Grignard + Ester

Grignard + Ester

Two equivalents of Grignard give a tertiary alcohol.

Alcohol + SOCl2

Alcohol + SOCl2

Converts an alcohol into an alkyl chloride.

Alcohol + PBr3

Alcohol + PBr3

Converts an alcohol into an alkyl bromide.

Secondary Alcohol Oxidation

Secondary Alcohol Oxidation

Chromic acid oxidizes it to a ketone.

Primary Alcohol Oxidation

Primary Alcohol Oxidation

Chromic acid oxidizes it to a carboxylic acid.