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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

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Treating a primary amide with thionyl chloride (SOCl2) 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
Transcribed Image Text:Treating a primary amide with thionyl chloride (SOCl2) 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
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