Chapter 15: Q86P (page 737)
Question: Is the acid-catalyzed hydrolysis of acetamide a reversible or an irreversible reaction? Explain.
Short Answer
Answer
Acid-catalyzed hydrolysis of acetamide is an irreversible reaction.
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Chapter 15: Q86P (page 737)
Question: Is the acid-catalyzed hydrolysis of acetamide a reversible or an irreversible reaction? Explain.
Answer
Acid-catalyzed hydrolysis of acetamide is an irreversible reaction.
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a. Which compound has the stretching vibration for its carbonyl group at the highest frequency: acetyl chloride, methyl acetate, or acetamide?
b. Which one has the stretching vibration for its carbonyl group at the lowest frequency?
Propose a mechanism that accounts for the formation of the product.

What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following?
a. a stronger base than the substituent that is attached to the acyl group
b. a weaker base than the substituent that is attached to the acyl group
c. similar in basicity to the substituent that is attached to the acyl group
Identify the major and minor products of the following reaction:

Rank the following amides from greatest reactivity to least reactivity toward acid-catalyzed hydrolysis:

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