In the IUPAC nomenclature, carboxylic acids are named by adding a suffix to the parent name of the longest chain. If the parent chain is noncyclic, you need to first find the longest carbon chain containing the -COOH group and change the … Read more
In this post, we will talk about the synthesis of amides using DCC and EDC coupling agents. Before getting into the details, let’s first discuss a couple of strategies for preparing amides without using any fancy coupling agent. First, considering … Read more
Both Grignard and organolithium reagents can be used to convert nitriles to ketones. The new C-C bonds are formed by nucleophilic addition of the organometallic reagents to the polar C-N triple bond. After protonation of the resulting anion, … Read more
Nitriles can be reduced to primary amines when treated with LiAlH4 or to aldehydes when a milder reducing agent such as DIBAL is used. Just like any other reduction reaction, an acidic or aqueous workup is needed to … Read more
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: … Read more
