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Reactivity of Amides

Last updated

Jan 23, 2023
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- Structure of Amides
- 1° Amides can be converted to Nitriles with Thionyl Chloride

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Amides are reasonably reactive, usually via an attack on the carbonyl breaking the carbonyl double bond and forming a tetrahedral intermediate. Thiols, hydroxyls and amines are all known to serve as nucleophiles. Owing to their resonance stabilization, amides are less reactive under physiological conditions than esters.

Topic hierarchy

1° Amides can be converted to Nitriles with Thionyl Chloride
1o Amides can be converted to nitriles by reaction by dehydration with thionyl chloride.
Amide to nitrile reduction mechanism
Conversion of Amides into Amines with LiAlH4
Amides can be converted to 1°, 2° or 3° amines using LiAlH4.
General Mechanism of Amide Reactions
Carboxylic acid derivatives are a group of functional groups whose chemistry is closely related. The main difference is the presence of an electronegative substituent that can act as a leaving group during nucleophile substitution reactions. Although there are many types of carboxylic acid derivatives known we will be focusing on just four: Acid halides, Acid anhydrides, Esters, and Amides.
Other Reactions of Amides
This page explains the reason for the lack of basic character in amides, and describes their dehydration to give nitriles, reaction with bromine and sodium hydroxide solution to form primary amines with one less carbon atom (the Hofmann degradation), and their reduction using LiAlH4.
Polyamides
Polyamides are polymers where the repeating units are held together by amide links. An amide group has the formula - CONH2. This page looks at the structures, formation, hydrolysis and uses of the polyamides, nylon and Kevlar.
The Hydrolysis of Amides
This page describes the hydrolysis of amides under both acidic and alkaline conditions. It also describes the use of alkaline hydrolysis in testing for amides.

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