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CHM 215 (2018) ORGANIC CHEMISTRY

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TUTORIAL 4
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Problems:

1. Design a synthetic pathway for the synthesis of the following compounds. Specify
the reagents clearly and show the structures of all products. More than one-step
may be required.

a) 2-Bromoethyl)benzene from benzene

b) Benzoic acid from benzene
c) Benzaldehyde from benzene

2. Propose a synthesis for each of the following compounds from benzene:

a) SO3H b) CO2H c) CO 2H d) Br

Br
NO2
Br CO 2H

e) f) CO2H g) h) Br

NO2

i)