Answer Happy

Draw the mechanisms and detail the steps for synthesis of the
following from benzene:
1. 3-chlorobenzene sulfonic acid 2. M-bromoaniline 3. P-bromo
isopropyl benzene 4. 3-amino-5-chloro benzene sulfonic acid.
Example of an explanation/ detailing the steps:
There are two substituents on the parent benzene ring; Bromine
and an acetyl amide. They are para to one another. Bromine can be
substituted on the benzene ring with a reaction with Br2 and FeBr3
. Br is an o,p director. There may be some ortho product as well,
but para should be favored in any additional reaction. Since we
only want 1 Br added to the ring, the catalyst should not be used.
To create the amide, there are several steps needed. NO2 can be
added to a ring then reduced to NH2 . (NO2 is m director; NH2 is
o,p) NH2 can be reacted with acetyl chloride in pyridine to
form the nucleophilic acyl substitution product. (The N is the
nucleophile attacking the carbonyl carbon of the acetyl chloride to
form the tetrahedral intermediate. Cl - is a good leaving
group.)