Reactions of Amides and Nitriles

You may use these summaries and problems but you may NOT download them for use at another site, nor may you charge for access to them. Copyright Linda M. Sweeting 1997

The following example reactions are organized by type, with references to text chapters. Links within these summaries (which may show up as boxes around reagents) will provide further information about the reagents and their other reactions. Return to Reaction Summary menu for other functional group choices.

Note that products are shown after neutralization with aqueous solution; neutralization of products is NOT shown here for simplicity.

Addition / Reduction


Other reagents: NaBH4 is not a strong enough reducing agent to do this reaction (unless it has help from an acidic reagent).
Nitrile reduction is essentially the same.
McMurry 24.6, 21.7, Fessenden 15.8C, Schmid 16.12, 16.15
To other syntheses of amines

Other reagents: NaBH4 is not a strong enough reducing agent to do this reaction (unless it has help from an acidic reagent).
McMurry 21.7, 24.7, Fessenden 15.8C, Schmid 16.12,
To other syntheses of amines

This reaction cannot be done with primary and secondary amides which are acidic enough to destroy the Grignard Reagent. Tertiary amides react like the nitrile shown here but may be sterically hindered from reaction with some Grignards.
This reaction produces an intermediate imine which is hydrolyzed to the ketone on neutralization in water.
Reference McMurry 19.6, 21.6, Schmid 16.15
To other syntheses of ketones

Addition / Elimination: Hydrolysis

+
Other reagents: H2O, OH-; primary, secondary and tertiary amides all undergo this reaction.
Nitrile hydrolysis is essentially the same; in fact, amides are intermediates in nitrile hydrolysis.
McMurry 21.6, Fessenden 15.8C, Schmid 15.11, 15.12
To other syntheses of carboxylic acids
To the main graphical reactions menu.
Last update February 1999