CMY 384 Tutorial 2 PDF

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CMY 384 tutorial on aromatic chemistry...

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Department of Chemistry CMY 384 – 2018 Problem Set A1.2 Show both the retrosynthetic analysis as well as the synthetic pathway for each product. (Do not use diazonium salts (Theme A2) as part of the syntheses for this problem set.) Question 1 Propose a synthesis for each of the following compounds from benzene: SO3H

O Br

a.

b.

NO2

NH2

d.

c.

NO2

e.

CO2H

Br

NH2

f.

CO2H

g.

Br

Br

Br

Cl

NH2 CO2H

i.

CO2H

h.

CO2H

k.

j.

l.

CO2H Br

NO2 NH2

m.

CO2H NO2

CH2OH

O o.

n. Br

Br

NH2

Br

NH2

OH

p.

Br

from phenol (single regioisomer)

from benzoic acid

Question 2 Attempted Friedel-Crafts acylation of benzene with t-BuCOCl and AlCl3 gives some of the expected ketone A as a minor product and also some t-butylbenzene B but the major product is the disubstituted product C. Explain how these compounds are formed and suggest the order in which the two substituents are added to form compound C.

Question 3 Challenge problem in ‘Problem Set Tut A1.1’...