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Chapter 21: Q.32P.d (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.

(d) succinic acid monomethyl ester

Short Answer

Expert verified

Answer

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

Step by step solution

01

Formation of succinic acid monomethyl ester

  • When an alcohol reacts with a succinic anhydride, only one of the carbonyl groups in the anhydride is converted to an ester group. The other is converted to carboxylic acid group.

As the above reaction acid is formed, it will not go into etser with methoxideformunder basic condition.

02

Step 2:Explanation

The anion of an acid is a good acid group formation and hence, anhydride is used in preference to acid chloride as succinic anhydride is cheap and easy to use.

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Most popular questions from this chapter

Show how you would convert the following starting materials to the indicated nitriles:

(a)phenylaceticacidphenylacetonitrile

(b)phenylaceticacid鈫�3-phenylpropionitrile

(c)p-chloronitrobenzenep-chlorobenzonitrile

Macrolide antibiotics, including erythromycin and azithromycin (), contain a large ring lactone. One of the largest ever reported is Gargantulide A, the structure of which was determined by the research group of Prof. William Gerwick of the Scripps Institution of Oceanography (Organic Letters, 2015, 17, 1377鈥�1380). Isolated from a Streptomyces bacterium, it kills pathogenic bacteria like MRSA and Clostridium difficile, but it proved too toxic to the test animals to continue further testing.

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(b) How many rings does this structure contain? How many atoms are in the largest ring?

(c) Many complex NMR experiments were used to determine the stereochemistry of most, but not all, of the chiral centers. How many chiral centers does the structure contain?

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)

(a)Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize

(i) benzyl acetate and

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(b)Propose a mechanism for each synthesis in part (a).

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

a.

b.

c.

d.

e.

f.

g.

h.

i.

j.

k.

l.

m.

n.

o.

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q.

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