What products are formed in the basic hydrolysis of the amide shown below with NaOH? O, NAOH/H,O

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter24: Amines And Heterocycles
Section24.1: Naming Amines
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What products are formed in the basic hydrolysis of the amide shown below with NaOH?
O, NAOH/H,O
Transcribed Image Text:What products are formed in the basic hydrolysis of the amide shown below with NaOH? O, NAOH/H,O
Expert Solution
Step 1-Introduction

The amide functional group is denoted as R-CO-NH2, where R can be alky, aryl, or hydrogen. When the amide constitutes the ring, it is termed as the lactam. The most common method to synthesis the amide is the reaction of the acid chloride with an amine. The amide linkage can be cleaved by treating with the base to furnish the acid and amine. The added base should be nucleophilic enough to react with the carbon of the carbonyl group. 

Step 2-Basic hydrolysis of amide

Reaction: 

Chemistry homework question answer, step 2, image 1

Explanation: 

The nucleophilic addition of the hydroxide ion to the amide 1 produces the oxygen anion 2. The shift of the electrons from the oxygen towards the carbon furnishes the amine anion and the acetic acid (3). The anion of amine abstracts the proton from the acetic acid to furnish the sodium acetate 4 and the cyclohexylamine 5.

 

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