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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

Rank the following compounds in order of decreasing frequency of the carbon-oxygen double bond stretch

Two products, A and B, are obtained from the reaction of 1-bromobutane with NH3 . Compound A reacts with acetyl chloride to form C, and compound B reacts with acetyl chloride to form D. The IR spectra of C and D are shown. Identify A, B, C, and D.

Question: Draw a structure for each of the following:

a. N,N-dimethylhexanamide

b. 3,3-dimethylhexanamide

c. Cyclohexanecarbonyl chloride

d. Propanenitrile

e. propionamide

f. sodium acetate

g. benzoic anhydride

h. b-valerolactone

i. 3-methylbutanenitrile

j. cycloheptanecarboxylic acid

k. benzoyl chloride

The intermediate shown here is formed during the hydroxide-ion-promoted hydrolysis of ester group. Propose a mechanism for the reaction.

Which is longer, the carbon鈥搊xygen single bond in a carboxylic acid or the carbon鈥搊xygen bond in an alcohol? Why?
See all solutions

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