Name: Glaizelle T. Leonoras Subject: Organic Chemistry

Course: Ph. D. in Science Education (Physical Science)
Professor: Vilma F. Templora, Ph.D.

Problem Set 6 Reactions of Electrophilic Aromatic Substitution

I. Give the major organic product(s) of each of the following reactions. If none is predicted,
write "N.R."

CH3

CH
CH3 +
1.

major CH2CH2C
N H3
H
2
NH
+
2
C
2.

H
3 C
C(C H
H3)3 3

3.
CO2
H

O
CH
O
3
+ B C
4.
N r H3
B O2
N
r
O2
C
O
l
H3C NHCCH
3
 5.

+
6.

C
CH3 CH3 S
I H
O
3

HO3S
B + I
3
HB
7.

r SO3H r

CH2
CH3
8.

N
H
2
9.

N.R.

(Friedel-Crafts reactions do not proceed in the presence of a deactivating group)

10.
O

H3OC O

CH3O + CH3O OCH3

11. COO
H

Choose the best reagent(s) from the list provided below for carrying outB the following conversions. Place
the letter of the reagent in the box beside the reaction number over therarrow. There is only one answer
for each reaction.

KMnO4, H3O+ ClCO(CH2)2CH3, AlCl3

Br2, FeBr3 CH3CH2CH2CH2Cl, AlCl3
Cl2, FeCl3 H2/Pd
CH3Cl, AlCl3 NBS, peroxides
HNO3, H2SO4 (CH3)3CCH2Cl
F-TEDA-BF4

b
1.

f
e

2.

d
a
c
3.

f
h

4.
i
5.

II. Propose syntheses to carry out each of the following conversions. Assume ortho and para
isomers can be separated.

1.

2.

3. Propose a synthesis for isobutylbenzene which avoids the problems of direct Friedel-Crafts
alkylation.