Chemistry Reference
In-Depth Information
b.
First make the ethylbenzene and then nitrate it:
H
+
+
H
2
C
CH
2
CH
2
CH
3
or
AlCl
3
+CH
3
CH
2
Cl
CH
2
CH
3
HONO
2
H
+
CH
2
CH
3
O
2
N
CH
2
CH
3
+
some
ortho
isomer
c.
Since the two substituents must end up in a
para
relationship, the first one
introduced into the benzene ring must be
para
-directing. Therefore,
brominates first and then nitrate.
d.
Alkyl groups are
ortho
,
para
-directing but the
−
SO
3
H group is
meta
-directing.
So, first we need to install the isopropyl group in a similar manner as part b,
perhaps using isopropyl chloride, (CH
3
)
2
CHCl, with AlCl
3
as a catalyst, and
then sulfonate the resulting isopropylbenzene (cumene).
e.
Arenes can be converted to substituted cyclohexanes by catalytic
hydrogenation.
