How are secondary amides made?

Secondary amides via an addition reaction between a nitrile and a carbonium ion in the presence of concentrated acids. A free radical homologation reaction between a terminal alkene and formamide. Base catalyzed reaction of esters with various amines to form alcohols and amides.

What are secondary amides?

Secondary amide (2o amide): An amide in which the nitrogen atom is directly bonded to two carbon atoms: the carbonyl group carbon plus one other carbon.

How do you identify a secondary amide?

Secondary amides are named by using an upper case N to designate that the alkyl group is on the nitrogen atom. Alkyl groups attached to the nitrogen are named as substituents. The letter N is used to indicate they are attached to the nitrogen. Try to draw a structure for the following compound: N,N-dimethylformamide.

How is a secondary amide different from a primary amide?

A primary (1°) amide has nitrogen attached to a single carbon; a secondary (2°) amide has the nitrogen attached to two carbons; a tertiary (3°) amide has the nitrogen attached to three carbons. When the amide nitrogen has substituents other than hydrogen, we specify them using the prefix N- to avoid confusion.

Which is the best way to prepare 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:

How are amides prepared from carboxylic acid anhydrides?

This page describes the preparation of amides from carboxylic acids, acyl chlorides (acid chlorides) and acid anhydrides. The carboxylic acid is first converted into an ammonium salt which then produces an amide on heating. The ammonium salt is formed by adding solid ammonium carbonate to an excess of the acid.

What kind of temperature is needed for amide synthesis?

Slightly higher temperatures are required for challenging starting materials. Aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines can be used. T. M. El Dine, W. Erb, Y. Berhault, J. Rouden, J. Blanchet, J. Org. Chem., 2015 , 80, 4532-4544.

How to make secondary amides from ketones and water?

This reacts with ketones to produce the corresponding sulfonyloxime, which in the presence of TsOH·H 2 O and water gives the corresponding amides. Nonetheless, this elegant method requires: (a) Brønsted acid and water as additives, (b) extended reaction times of 24 h, (c) column chromatographic purification.