Chapter 21: Q-21-21-5P (page 688)
Predict the products of the following nucleophilic acyl substitution reactions:

Short Answer
The products of each reaction are as shown below:

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Chapter 21: Q-21-21-5P (page 688)
Predict the products of the following nucleophilic acyl substitution reactions:

The products of each reaction are as shown below:

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The step-growth polymer nylon 6 is prepared from caprolactam. The reaction involves the initial reaction of caprolactam with water to give an intermediate open-chain amino acid, followed by heating to form the polymer. Propose a mechanism for both steps, and show the structures of nylon 6.

21-70 Treatment of a carboxylic acid with trifluoroacetic anhydride leads to anunsymmetrical anhydride that rapidly reacts with alcohol to give an ester.
(a) Propose a mechanism for the formation of the unsymmetrical anhydride.
(b) Why is the unsymmetrical anhydride unusually reactive?
(c) Why does the unsymmetrical anhydride react as indicated ratherthan giving a trifluoroacetate ester plus carboxylic acid?
If the following molecule is treated with acid catalyst, an intramolecular esterification reaction occurs. What is the structure of the product? (Intramolecular means within the same molecule.)

What ester and what Grignard reagent might you start with to prepare the following alcohols?
a.

b.

c.

21-75 One frequently used method for preparing methyl esters is by reactionof carboxylic acids with diazomethane,
The reaction occurs in two steps: (1) protonation of diazomethane bythe carboxylic acid to yield methyldiazonium ion,, plus a carboxylate ion; and (2) reaction of the carboxylate ion with .
(a) Draw two resonance structures of diazomethane, and account forstep 1.
(b) What kind of reaction occurs in step 2?
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