Assignment 1 CHE 495

1. Design syntheses of compounds I and II. Use only the starting materials provided in the
square brackets (you may use more than 1 material).
I.

II.

HO

O
Br

HC CH

Br

Br

2. Compound A has the formula C10H16. On catalytic hydrogenation over palladium, it

reacts with only 1 molar equivalent of H2. Compound A also undergoes reaction with
ozone, followed by zinc treatment, to yield a symmetrical diketone, B (C10H16O2). By
showing the reaction steps, predict the structures of A and B.
3. At what position, and on what ring, would you expect the following substances to
undergo electrophilic substitution?

4. 4-bromo-3-nitrobiphenyl is to be synthesized from benzene. Select the most appropriate

reaction method from the three (3) schemes presented below and justify your answer.
O 2N
Br

benzene

4-bromo-3-nitrobiphenyl

Method 1
O 2N
HNO3

Pd(OAc)2,
CoCat

H2SO4

AcOH,
130oC

O 2N

O 2N
Br2

Br
FeBr3

Method 2
O 2N

Pd(OAc)2,
CoCat

Br2

AcOH,
130oC

FeBr3

HNO3
Br

Br

H2SO4

Method 3
Br2
Br
FeBr3

O 2N

Pd(OAc)2,
CoCat

HNO3
Br

AcOH,
130oC

H2SO4

Br