Chapter 21: Q36P-a (page 1129)
Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.
Short Answer
Synthetic transformation for N-ethylbenzamide to benzylethylamine is show as,

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Chapter 21: Q36P-a (page 1129)
Show how you would accomplish the following synthetic transformations. You may use any necessary reagents.
Synthetic transformation for N-ethylbenzamide to benzylethylamine is show as,

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When ethyl 4-hydroxybutyrate is heated in the presence of a trace of a basic catalyst (sodium acetate), one of the products is a lactone. Propose a mechanism for the formation of this lactone.
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.

p.

q.

r.

Show how you would accomplish the following syntheses using amides as intermediates.
You may use any necessary reagents.
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 synthesize the following esters from appropriate acyl chlorides and alcohols.
(a) ethyl propionate
(b)phenyl 3-methylhexanoate
(c)benzyl benzoate
(d)cyclopropyl cyclohexanecarboxylate
(e)tert-butyl acetate
(f) diallyl succinate
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