CHEM 2061 Fall 2008 EXAM #3 Name ______________________

1. (12 pts, 4 each) A) Give the structure of the major organic product in each of the following
SUBSTITUTION reactions, and B) predict whether the mechanism will be predominantly 1st order
(SN1) or second order (SN2). Be sure to show the correct stereochemistry of the product when necessary.
If the product is a racemic mixture, draw both enantiomers.

H Br HO-
a)
CH3

H3C OTs CH3CH2OH

b)

_
CH Cl H C C Li+
c) CH3CH 2
CH3

2. (10pts, 5 each) A) Give the structure of the major organic product in each of the following
elimination reactions, and B) predict whether the mechanism will be predominantly first order (E1) or
second order (E2). BE SURE TO SHOW THE CORRECT STEREOCHEMISTRY OF THE
PRODUCT WHEN NECESSARY.

a)
CH3OH
CH3CH2
CH3
Br

b) CH3
Br CH3 H3C C O K+
CH2CH3 CH3

H CH3

3. (3 pts) Which of the following is the best solvent for a SN1 reaction?
a) hexane b) methanol c) acetone d) dichloromethane
4. (8 pts) Write the complete mechanism for the following acid-catalyzed hydration reaction of 2-
methylpropene.
H3C H OH
H2SO4
C C H3C C CH3
H3C H
H20 CH3

5. (4 pts) Give the IUPAC name of the following compound. Be sure to use E-Z and R-S
nomenclature if necessary.
CH3

H3C H
6. (5 pts) Give the major product of the following reaction:
CH3
H3C C O
CH3

OTs
7. (6 pts, 3 each) Will the following reactions go faster if the concentration of the nucleophile is
increased? (Write Yes if the reaction will go faster, No if it doesnt go faster).

a)
H Br MeO H
H3C O
+

Br CH3
b) O O
CH3 CH3
+ H3C O O
8. (12 pts) Consider the following E2 elimination reactions of menthyl chloride and neomenthyl
chloride:
A) Using mechanistic reasoning, EXPLAIN WHY menthyl chloride gives only 2-menthene as its
E2 elimination product.
B) Explain why 3-menthene (rather than 2- menthene) is the major product in the E2 elimination
of neomenthyl chloride.
H
CH3
CH3 CH3CH2 O
H3C
H3C Cl
CH3
CH3
H
2-menthene (100% yield)
menthyl chloride
H
CH3
CH3CH2 O
CH3 H3C
H3C H CH3
CH3
Cl 3-menthene (78% yield)

neomenthyl chloride +
2-menthene (22% yield)
9. (12 pts) Bromoetherification, the addition of the elements Br and OR to a double bond, is a
common method for constructing rings containing oxygen atoms. Draw a stepwise mechanism for
the following INTRAMOLECULAR bromoetherification reaction. Hint: the mechanism is
analogous to that of bromohydrin formation when Br and OH are added to an alkene double bond
using Br2 and H2O).

Br2 O Br
+ HBr
HO

10. (28 pts, 4 each) Give the structure of the major organic product of each of the following
reactions. Clearly indicate stereochemistry where appropriate. If the major product is a pair
of enantiomers, only draw one of the two structures.
conc.
a) H2SO4
OH
heat

Br2
CH3
b)
CCl4

CH2CH3 H2
c)

Pt
CH2CH3
d) H3C CH2CH3 1) O3

H CH2CH3 2) CH3SCH3
3) H30+

e) OsO4

H2O2
CH3

1) BH3.THF
f)
2) H2O2, NaOH
H2O

O
Cl H
O O
g)

CH2Cl2