Chemistry 8A

Assignment 9-2 (Chapter 9) Answer Key

Alkenes - Addition Reactions

1.

Provide the primary product of each of the following alkene additions.

Br

HBr

HBr

Br

Cl

HCl

2.

Provide an alkene starting material which could yield the product shown under the indicated
conditions. There may be more than one answertry to think of all the possibilities!

or

or

HBr

Br

Br

HBr

HCl
Cl

Lecture Assignment 9-2 (Page 1of 5)

3.

For each of the reactions shown below, draw the structure of the major organic product.
Clearly show all stereochemistry.

OH

OH
OH
OH

CH3
OH
OH
HO
H
H
CH3

OH
OH

OH

Lecture Assignment 9-2 (Page 2of 5)

2.

Predict the product(s) for the following reactions (addition/elimination). Indicate stereochemistry
in the product.

3.

Predict the reactant (bicyclic molecule) and the reagents to yield the following products.

Lecture Assignment 9-2 (Page 3of 5)

4.

Predict the major product(s) of the following reactions. Indicate the correct stereochemistry
when necessary.

OH

1.

Br2
H2O

OH
Br

Br
OH exo diol

2.

OH

1)

OsO4 / pyridine
2) NaHSO3 / H2O

OHC

HIO4

CHO

OH
OH

3.

endo diol
Cl
Cl

CHCl3
KOH
4.
1)

Hg(OAc)2
H2O/THF
2) NaBH4

OH

5.
1)
2)

hot KMnO4
H3O

HO
6.

Br
NaOMe / MeOH
heat

major
minor
E2 elimination -Br and H have to be antiperiplanar
Lecture Assignment 9-2 (Page 4of 5)

Lecture Assignment 9-2 (Page 5of 5)