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Chapter 21: Q.32P.C (page 1123)

Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydride might be preferable to an acid chloride.

(c) phthalic acid monoamide

Short Answer

Expert verified

Answer

The use of anhydride to synthesize the given compound is given below.

Step by step solution

01

formation of phthalicmonoamide.

  • When ammonia NH3 reacts with cyclic anhydride, only one carbonyl group in the anhydride is converted to an amide group. The other is converted to carboxylic acid group and monofunctionalized derivative NH3.
02

Anhydride might be preferable to an acid chloride.

In the case of acylation, an Acyl group i.e. group replaces the H atom in the benzene ring. Acetic anhydride is preferred for acylation reaction because of its ease of availability. Moreover, it is easy to handle and cheap compared to acetyl chloride.

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Most popular questions from this chapter

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.

(a)N,N-dimethylacetamide

(b)acetanilide(PhNHCOCH3)

(c)cyclohexanecarboxamide

(d)

Two widely used pain relievers are aspirin and acetaminophen. Show how you would synthesize these drugs from phenol.

Aspirin Acetaminophen

(a)Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.

(b) Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.

(c)Propose a secondmechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the otheroxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.

(d)Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.

(e)Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an SN2 reaction?

Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.

d.Ph2CHOH

What characteristics of the phenyl propanoate spectrum rule out an aldehyde or carboxylic acid functional group giving the absorption at 1730cm-1?
See all solutions

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