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Chapter 21: Q35-g (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.

g. PhCH2COOHCH32

Short Answer

Expert verified

The synthesis of the given compound is given below.

Step by step solution

01

Use TsCI, pyridine and KCN

In this reaction, TsCI,pyridineandKCNis used to convert an alcohol into cyanide. In this reaction alcohol group, Since OH- is not good leaving, it is converted into OTs, and then Cyanide anion removes the -OTs group into cyanide.

Cyanide formed in step 1 gets hydrolysis, and carboxylic acids are formed.

02

Formation of final product PhCH2COOHCH32

When carboxylic acid reacts with secondary alcohol in the presence of an acid, then its ester is formed.

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Most popular questions from this chapter

Show how you would accomplish the following syntheses using amides as intermediates.

You may use any necessary reagents.

(b)pyrrolidine鈫�N-ethylpyrrolidine

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.

Which of the following proposed reactions would take place quickly under mild conditions?

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.

(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?

(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?
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