Nitriles can be hydrolyzed to carboxylic acids in acidic aqueous solutions, and to carboxylate salts with base-catalyzed hydrolysis: In both cases, the transformation consists of two main parts: conversion of the nitrile to an amide and hydrolysis of … Read more
Amides As you know from the functional groups, amides are the “combination” of the carbonyl and amines: Depending on the number of carbons connected to the nitrogen, we have primary, secondary and tertiary amides. Notice that the carbonyl carbon is … Read more
Amides can be reduced to amines by LiAlH4: Remember that the reduction of all the other carboxylic acid derivatives containing a carbonyl group produces alcohols: Another exception is the nitriles, but these do not contain a … Read more
Primary amides can be converted to nitriles by strong dehydrating agents such as SOCl2, P2O5, and POCl3: Before going into the mechanisms of these reactions. Let’s first address one important question you might be wondering about. Why is … Read more
Base-Catalyzed Hydrolysis of Amides Amides are the least reactive derivatives of carboxylic acids because the conjugate base of an amine, formed in a nucleophilic substitution reaction, is a poor leaving group. For example, in the reaction with a hydroxide, we … Read more
Preparation of Amides Amides can be prepared from acyl chlorides, esters, and carboxylic acids. The most straightforward should be the reaction with acid chlorides since they are the most reactive carboxylic acid derivatives, and amines are good nucleophiles too. This … Read more
Preparation of Anhydrides Anhydrides are prepared by dehydration of carboxylic acids either at extremely high temperatures (800 oC) or by using P2O5 as a dehydrating agent: For most carboxylic acids are not compatible with excessive heating, and even … Read more
This article summarizes the main reactions of esters with associated practice problems. We covered the mechanism and other details about each reaction, so if you need to go over them, click on the corresponding links. Let’s start with the hydrolysis … Read more
Esters can be converted into primary, secondary, and tertiary amides by an aminolysis reaction with ammonia, primary amine, and a secondary amine, respectively: The reaction goes by a nucleophilic addition-elimination mechanism, and alkoxy groups (RO–), being poor leaving … Read more
Reduction of Acyl Chlorides to Alcohols Acid chlorides can be reduced to alcohols by lithium aluminum hydride (LiAlH4) and sodium borohydride (NaBH4). In both reactions, there is an aldehyde intermediate formed, and therefore, the reducing agent is used … Read more
