CHM 201
Chapter 10 Exam Problems
1. The allylic bromination of the alkene below with NBS gives four different
products. Draw the two initially formed free radical intermediates together
with any applicable resonance structures and the four products. Which
product do you expect to be the major one and which is formed in lowest yield?
Identify them both.
CH3
CH3
NBS in CCl4
hν
CH3
CH3
CH2
CH3
CH2
CH3
CH3
CH3
.
.
.
.
CH3
CH3
Br
CH3
CH3
Br
BrCH2
CH3
CH2
CH3
Br
AA'
BB'
AA'
B
B'
major
+
+
lowest yield
