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Chapter 21: Q35-h. (page 1126)

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

h.

Short Answer

Expert verified

The synthesis of the given compound is given below.

Step by step solution

01

Use of Grignard reagent.

In the above reaction, the Grignard reagent is used to convert an ester to alcohol, and an excess of Grignard reagent is used because of the ester.

When ester reacts with the Grignard reagent in the first product, there is the formation of ketone. This ketone reacts with another molecule of Grignard reagent and there is a formation of alcohol.

02

Formation of  PhCH2-COH (CH2CH3)2

When the Grignard reagent is used in excess, the ester is converted into alcohol after hydrolysis. Here, ester PhCH2-COOH (CH3)2 in the presence of Grignard reagent CH3CH2MgBr in excess after hydrolysis gives PhCH2-COH (CH2CH3)2 alcohol.

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Most popular questions from this chapter

Complete the mechanism for this acid-catalyzed transesterification by drawing out all the individual steps. Draw the important resonance contributors for each resonance stabilized intermediate.

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

Draw structures to correspond with the following common and systematic names:

(a)phenyl formate

(b)cyclohexyl benzoate

(c)cyclopentyl phenylacetate

(d)N-butylacetamide

(e)N,N-dimethylformamide

(f)benzoic propionic anhydride

(g)benzamide

(h)-hydroxyvaleronitrile

(i)-bromobutyryl chloride

(j)-butyrolactone

(k)phenyl isocyanate

(l)cyclobutyl ethyl carbonate

(m)-caprolactam

(n)trichloroacetic anhydride

(o)ethyl N-methyl carbamate

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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