# Making Amides from Nitriles


The hydrolysis of nitriles is a satisfactory method for preparation of unsubstituted amides and is particularly convenient when hydrolysis is induced under mildly basic conditions by hydrogen peroxide:

For the preparation of amides of the type $$\ce{R_3CNHCOR}$$, which have a tertiary alkyl group bonded to nitrogen, the Ritter reaction of an alcohol or alkene with a nitrile or hydrogen cyanide is highly advantageous. This reaction involves formation of a carbocation by action of strong sulfuric acid on an alkene or an alcohol (Equation 1), combination of the carbocation with the unshared electrons on nitrogen of $$\ce{RCN}$$ (Equation 2), and then addition of water (Equation 3). We use here the preparation of an $$\ce{N}$$-tert-butylalkanamide as an example; $$\ce{RC \equiv N}$$ can be an alkyl cyanide such as ethanenitrile or hydrogen cyanide itself:

$$\tag{1}$$

$$\tag{2}$$

$$\tag{3}$$

This reaction also is useful for the preparation of primary amines by hydrolysis of the amide. It is one of the relatively few practical methods for synthesizing amines with a tertiary alkyl group on the nitrogen:

## Contributors

John D. Robert and Marjorie C. Caserio (1977) Basic Principles of Organic Chemistry, second edition. W. A. Benjamin, Inc. , Menlo Park, CA. ISBN 0-8053-8329-8. This content is copyrighted under the following conditions, "You are granted permission for individual, educational, research and non-commercial reproduction, distribution, display and performance of this work in any format."

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