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Making Amides from Nitriles

  • Page ID
    37193
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    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:

    Roberts and Caserio Screenshot 24-3-3.png

    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:

    Roberts and Caserio Screenshot 24-3-4.png\(\tag{1}\)

    Roberts and Caserio Screenshot 24-3-5.png\(\tag{2}\)

    Roberts and Caserio Screenshot 24-3-6.png\(\tag{3}\)

    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:

    Roberts and Caserio Screenshot 24-3-7.png

    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."


    Making Amides from Nitriles is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by LibreTexts.

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