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12 MECHANISMS

Carboxylic Acids & Derivatives

Nitrile Hydrolysis (Acid)

Nitrile Hydrolysis (Acid)

A nitrile hydrolyzes to a carboxylic acid.

Nitrile Hydrolysis (Base)

Nitrile Hydrolysis (Base)

Base hydrolyzes a nitrile to a carboxylate.

Grignard Carboxylation

Grignard Carboxylation

A Grignard reagent plus CO2 gives a carboxylic acid.

Ester to Amide

Ester to Amide

An amine converts an ester into an amide.

Fischer Esterification

Fischer Esterification

Acid and alcohol form an ester reversibly.

Saponification

Saponification

Base hydrolyzes an ester to a carboxylate.

Ester Hydrolysis (Acid)

Ester Hydrolysis (Acid)

Acid hydrolyzes an ester to acid plus alcohol.

Ester Reduction (LAH)

Ester Reduction (LAH)

LiAlH4 reduces an ester to a primary alcohol.

Ester + Grignard

Ester + Grignard

Two equivalents of Grignard give a tertiary alcohol.

Amide Hydrolysis (Acid)

Amide Hydrolysis (Acid)

Acid hydrolyzes an amide to a carboxylic acid.

Amide Hydrolysis (Base)

Amide Hydrolysis (Base)

Base hydrolyzes an amide to a carboxylate.

Grignard + Nitrile

Grignard + Nitrile

A Grignard adds to a nitrile to form a ketone.