Depto. Química Orgánica

CARBOXYLIC ACID PREPARATION BY NITRILE HYDROLYSIS

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15/07/2017
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Preparation of carboxylates from nitriles
Nitriles hydrolize in basic medium leading to carboxylic acids. 
Therefore, the introduction of a nitrile group - by means of a SN reaction with cyanide of a compound with a good leaving group - is an excellent method to obtain a carboxylic acid.
Image Remember that the nucleophilic substitution reactions cannot be always achieved depending on the structure of the R group.
Click here to recall how the aliphatic SN worked.
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Another interesting possibility is the formation of a cyanhydrin, by addition of cyanide to an aldehyde.
Ulterior nitrile hydrolysis renders alpha-hydroxyacids.
Click here to refresh what a cyanhydrin is.
Click here to anticipate the mechanism of nitrile hydrolysis that pertains to the next chapter.