Reactions of Esters

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; neutralization of products is NOT shown here for simplicity.
Thioesters behave like esters, but are somewhat more reactive.

Addition / Reduction

Other reagents: H2 / Pt, or similar catalyst; NaBH4 is a weaker reducing agent and reacts slower with esters than with ketones so that selective reductions can be done.
McMurry 21.5, Fessenden 15.5C, Schmid 15.17
To other syntheses of alcohols
Note that two moles of Grignard reagent are required to do this reaction. The product from addition of one mole of Grignard is a ketone which also reacts with Grignard. If two moles of Grignard are not present, incomplete reaction yields a mixture of products and starting materials.
McMurry 21.5, Fessenden 7.3D, 15.5C, Schmid 16.13
To other syntheses of alcohols

Addition / Elimination

This reaction is known as hydrolysis.
Base-catalyzed hydrolysis, i.e. with H2O, OH-, is known as saponification
McMurry 21.6, Fessenden 15.5C, Schmid 15.11, 15.12
To other syntheses of carboxylic acids
This reaction is known as interesterification or trans-esterification.
Other reagents: any other alcohols
McMurry 21.5, Fessenden 15.5C, Schmid 16.9
McMurry 21.5, Fessenden 15.5C, Schmid 16.9
To other syntheses of amides
To synthesis of esters
To the main graphical reactions menu.
Last update April 1999