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Chapter 21: Q.33P (page 1123)

Propose a mechanism for the formation of 9-hydroxynonanoic acid lactone, as show in the preceding figure.

Short Answer

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Answer

A mechanism for the formation of 9-hydroxynonanoic acid lactone is shown below.

Step by step solution

01

Concept introduction of Lactones

Lactones are the cyclic esters of hydroxycarboxylic acids. Simple lactones that contains five and six-membered rings are more stable than the open-chain hydroxyl acids. Lactones are formed spontaneously under acidic conditions.

02

Formation of 9-hydroxynonanoic acid lactone

Lactone is formed by the intermolecular esterification of hydroxycarboxylic acids that take place simultaneously and result in the formation of 9-hydroxynonanoic acid lactone.

Mechanism

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Most popular questions from this chapter

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.

e. PhCH2OH

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

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, 1377–1380). 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.

(a) Identify the lactone that makes this a macrolide structure.

(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 accomplish the following synthetic transformations. You may use any necessary reagents.(d)γ-aminobutyricacid→pyrrolidine

Show how you would synthesize each compound, starting with an ester containing nomore than eight carbon atoms. Any other necessary reagents may be used.

b. (PhCH2)2CHOH
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