Mark Bishop

Analytical Chemistry and

Signal Acquisition/Analysis



Functional Derivatives of Carboxylic Acids

Acid chlorides

Preparation

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Reactions

Conversion into acids and derivatives

   Hydrolysis

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   Ammonolysis

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   Alcoholysis

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Formation of ketones

Friedel-Crafts Acylation

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Reaction with organocadmium compounds

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Reduction to aldehydes

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Anhydrides

Preparation

Ketene intermediate sec 20.9

Reactions

Hydrolysis

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Ammonolysis

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Alcoholysis

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Friedel-Crafts Acylation

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Amides

Preparation

See reactions of acid chlorides and anhydrides above.

Reactions

Hydrolysis

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Conversion to imides

Certain cyclic anhydrides undergo ammonolysis to yield products that contain both acid and amide functionality. Heating these compounds may produce an imide. For example:

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Hofmann degradation

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Esters

Preparation

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Can also be made from acid chlorides and anhydrides (see above).

Reactions

Hydrolysis

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Ammonolysis

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Transesterification

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Reaction with Grignard reagents

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Reduction to alcohols

    Hydrogenation

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   Chemical reduction

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Claisen condensation: (See reactions involving carbanions)

Carbonic Acid and its derivatives

Carbon dioxide dissolves in water to for carbonic acid.

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Carbonic acid has several important derivatives (which are in fact not actually synthesized from carbonic acid itself).

Phosgene or carbonyl chloride

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Urea or Carbamide

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Cyanamide

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ID may be exposed