ST.

JOHN’S COLLEGE JUNIOR COLLEGE

ORGANIC CHEMISTRY 234
TOPIC: ALKENES

1. Propene reacts with hydrogen bromide forming 2-bomopropane as the major product.
a) Write an equation for this reaction.

b) Outline the mechanism for this reaction, showing the structure of the intermediate
carbocation formed.

c) Give the structure of the alternative carbocation which could be formed in the
reaction between propene and hydrogen bromide.

d) Explain why the formation of 1-bromopropane is not favored.

2. What does it mean for something to be conjugated? Why are conjugated double bonds
more stable than non-conjugated double bonds?

3. What allows conjugated dienes to form two addition products?

 4. What is meant by “electrophilic addition to a diene is temperature
dependent”? Why?

5. What are the characteristics of the Diels-Alder reaction? (mechanism, bonds formed and
broken, nucleophile and electrophile, required geometry) Provide an example

GIVE THE MAJOR ORGANIC PRODUCT OF THE REACTION, PAYING PARTICULAR ATTENTION TO REGIO-
AND STEREOCHEMICAL OUTCOME

6.

HCl

Cl2, H2O

CH3 BH3 , THF H2O2 , OH-

 OsO4
H2O2

O3
Zn, H3O+

CH3 H3O+

\
Give a detailed mechanism for the following reactions

a. HCl
b.
Hg(OAc)2, H2O NaBH4

c.