Treating a primary amide with thionyl chloride (SOCI2) is another way of synthesizing a nitrile. Draw a mechanism for this transformation. Hints: . ● The first few steps are essentially identical to synthesis of an acyl chloride from a carboxylic acid. All steps are one of the following: proton-transfer to make HCl; nucleophilic addition; nucleophilic elimination. Do not deprotonate nitrogen unless it has a + formal charge. NH₂ CI O=S: CI -CEN + SO₂ + 2HCI

Treating a primary amide with thionyl chloride (SOCI2) is another way of synthesizing a nitrile. Draw a mechanism for this transformation. Hints: . ● The first few steps are essentially identical to synthesis of an acyl chloride from a carboxylic acid. All steps are one of the following: proton-transfer to make HCl; nucleophilic addition; nucleophilic elimination. Do not deprotonate nitrogen unless it has a + formal charge. NH₂ CI O=S: CI -CEN + SO₂ + 2HCI

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.47P

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