Functional derivatives of carboxylic acids – characteristics and types. Main chemical properties.
Introduces the acid derivatives (salts, acyl chlorides, amides, esters, thioesters, anhydrides and phosphate esters) that share the acyl group, and explains how their reactivity ranks from acyl chlorides down to carboxylic acids. It then covers hydrolysis, alcoholysis and ammonolysis, and the structure and biological role of soaps, fats and oils. The note closes with phosphate esters, diphosphate and triphosphate esters, and why ATP is so energy-rich.
Topic 29 of 47 in the MU Pleven syllabus for Chemistry (Medicine, Year 1). The free AceMed note covers it in 6 sections, about 1,395 words (10 min of reading), with 15 flashcards.
In this note
FUNCTIONAL DERIVATIVES OF CARBOXYLIC ACIDS. MAIN CHEMICAL PROPERTIES
I. General characteristics
II. Reactivity
III. Typical reactions
IV. Specific characteristics and biological importance
Organophosphate esters and anhydrides
I. General characteristics
Carboxylic acids are the parents for several families that collectively are called acid derivatives. They include:
They’re called acid derivatives because they canbemade from acids and they can be hydrolyzed back to the acids.
The acyl group, a carboxyl group minus OH, occursinall of them.
II. Reactivity
The reactions,by which the acid derivatives are made as well as the reactions of the derivatives themselves, either in vitro or in vivo, generally occur as acyl group transfer reactions (nucleophilicsubstitution)
The ability to transfer an acyl group however, varies widely among the acidderivatives
Carboxylic acids, which have a poor leaving group (OH) require acid catalysis in order to undergo nucleophilic substitution, whereas acyl chlorides, which have a good leaving group (Cl) require no catalysis. The reactions of acid anhydrides and esters are generally slow unless catalysis (acid or base) is employed.
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