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Chapter 21: Q28E (page 726)

How would you prepare the following compounds starting with an appropriate carboxylic acid and any other reagents needed? (Reddish brown = Br.)

a.

b.

Short Answer

Expert verified

Preparation of the given compounds can be shown as

a.

b.

Step by step solution

01

Preparation of Compound a

Acid reacts with alcohol to produce ester.

02

Preparation of Compound b

Acid reacts with ammonia or amines to produce amide. The compound given in b can be formed as

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Most popular questions from this chapter

21-51 What product would you expect to obtain from Grignard reaction ofan excess of phenylmagnesium bromide with dimethyl carbonate, CH3OCO2CH3?

Why is the saponification of an ester irreversible? In other words, why doesn’t treatment of a carboxylic acid with an alkoxide ion yield an ester?

21-36 When 4-dimethylaminopyridine (DMAP) is added in catalytic amountsto acetic anhydride and an alcohol, it significantly increases the rate of ester formation. The process begins with a reaction between acetic anhydride and DMAP to form a highly reactive acetylpyridinium intermediate that is more reactive than acetic anhydride itself. Propose a mechanism for this process that includes the formation and reaction of the acetylpyridinium intermediate.

The hydrolysis of a biological thioester to the corresponding carboxylate is often more complex than the overall result might suggest. The conversion of succinyl CoA to succinate in the citric acid cycle, for instance, occurs by initial formation of an acyl phosphate, followed by reaction with guanosine diphosphate (GDP, a relative of adenosine diphosphate [ADP]) to give succinate and guanosine triphosphate (GTP, a relative of ATP). Suggest mechanisms for both steps.

Predict the product(s) of the following reactions:
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