Chapter 21: Q-21-21-12P (page 699)
Question: How could you prepare the following amides using an acid chloride and an amine or ammonia?
- N,N-Dimethylbenzamide
- Propanamide
Short Answer
(a)
(b)

(c)
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Chapter 21: Q-21-21-12P (page 699)
Question: How could you prepare the following amides using an acid chloride and an amine or ammonia?
(a)
(b)

(c)
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What product would you expect from reaction of one equivalent of methanol with a cyclic anhydride, such as phthalic anhydride (1,2-benzenedicarboxylic anhydride)? What is the fate of the second 鈥渉alf鈥 of the anhydride?

Why is the saponification of an ester irreversible? In other words, why doesn鈥檛 treatment of a carboxylic acid with an alkoxide ion yield an ester?
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?
Predict the products of the following nucleophilic acyl substitution reactions:

Explain the observation that attempted Fischer esterification of 2,4,6-trimethyl benzoic acid with methanol and HCL is unsuccessful. No ester is obtained, and the acid is recovered unchanged. What alternative method of esterification might be successful?
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