Hydrolysis of a nitrile such as ethanenitrile with dilute acid gives

Correct answer: D. a carboxylic acid with the same number of carbon atoms as the nitrile

  • A. an amine
  • B. an aldehyde
  • C. an alcohol
  • D. a carboxylic acid with the same number of carbon atoms as the nitrile

Explanation

The carbon of the nitrile group becomes the carbon of the carboxyl group, so hydrolysing ethanenitrile gives ethanoic acid and ammonia is released as its salt. Since the nitrile itself was made by adding cyanide to an alkyl halide with one fewer carbon, the two steps together lengthen the chain by one. Reduction rather than hydrolysis of a nitrile gives a primary amine.

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About Nomenclature, Structure and Preparation

Carboxylic acids are prepared by oxidising primary alcohols or aldehydes, hydrolysing nitriles, esters and amides, and carbonating suitable organometallic compounds. Their structures, IUPAC naming, resonance stabilisation and acidic character explain why carboxylic acids differ from alcohols and phenols, despite all containing oxygen and hydrogen.

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