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Chapter 15: Q86P (page 737)

Question: Is the acid-catalyzed hydrolysis of acetamide a reversible or an irreversible reaction? Explain.

Short Answer

Expert verified

Answer

Acid-catalyzed hydrolysis of acetamide is an irreversible reaction.

Step by step solution

01

Product formed by acid-catalyzed hydrolysis of acetamide

When acetamide undergoes hydrolysis in the presence of acid, it forms acetic acid and

ammonium ion. The reaction is given below.

02

Identifying reversible or irreversible

The reaction is an irreversible reaction because acetic acid cannot react with ammonium ion since it is not a nucleophile. Moreover, of ammonium ion is greater than that of acetic acid. Thus, they are not in their reactive acidic or basic form.

If the solution obtained is acidic, then both acetic acid and ammonium ion will be in its acidic form, and ammonium ion cannot act as nucleophile.

Acidic constituents

Similarly, if the solution obtained is basic, then both will be in their basic form, and the nucleophile cannot attack the carboxylate ion.

Basic constituents

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Most popular questions from this chapter

Phosgene (COCl2) was used as a poison gas in World War I. What product would be formed from the reaction of phosgene with each of the following reagents?

a. one equivalent of methanol

b. excess methanol

c. excess propylamine

d. excess water

a. What is the product of the reaction of acetyl chloride withHO-? ThepKaof HCl is -7; thepKaofH2Ois 15.7.

b. What is the product of the reaction of acetamide withHO-? ThepKaofNH3is 36; thepKaofH2Ois 15.7.

An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product isformed? Explain.

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

When a compound with molecular formula C11H14O2undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following H1NMR spectrum. Identify the compound.
See all solutions

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