Hydrolysis of nitriles with aqueous acid to give carboxylic acids
Description: Addition of water and acid to a nitrile leads to formation of a carboxylic acid.
This page is available to MOC Members only.
Sign up here for about 30 cents/ day!
Real-World Examples:
Org. Synth. 1925, 5, 69; Org.
DOI Link: 10.15227/orgsyn.005.0069
Click to Flip
Org. Synth. 1938, 18, 50
DOI Link: 10.15227/orgsyn.018.0050
Click to Flip
Org. Synth. 1931, 11, 96
DOI Link: 10.15227/orgsyn.011.0096
Click to Flip
Org. Synth. 1947, 27, 1
DOI Link: 10.15227/orgsyn.027.0001
Click to Flip
Org. Synth. 1944, 24, 96
DOI Link: 10.15227/orgsyn.024.0096
Click to Flip
Org. Synth. 1952, 32, 92
DOI Link: 10.15227/orgsyn.032.0092
Click to Flip
Would hydrolysis of nitriles with aqueous acid to give amides first?
Would nitriles become amides first, then carboxylic acids?
Thank you very much.
Yes, that is absolutely correct. It’s possible to stop it at the amide stage.
do you have a base-promoted version of hydrolysis as well?
Base promoted hydrolysis of amides is hard, because eventually the nitrogen has to leave as an anion, and species like H2N- and R2N- are very very strong bases. It can be done, however. https://pubs.acs.org/doi/abs/10.1021/ja00421a046
missing a H on NH4+ -OSO3 in product??
Oops – yes. Sorry, let me fix that. Thanks for spotting
do you have a convenient metod based on articles for this reaction??