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

“No” if it doesn’t go faster). a) H Br MeO H H3C O + Br CH3 b) O O CH3 CH3 + H3C O O .4. CH3 H3C H 6. H3C H OH H2SO4 C C H3C C CH3 H3C H H20 CH3 5. (5 pts) Give the major product of the following reaction: CH3 H3C C O CH3 OTs 7. (8 pts) Write the complete mechanism for the following acid-catalyzed hydration reaction of 2- methylpropene. (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. (4 pts) Give the IUPAC name of the following compound. Be sure to use E-Z and R-S nomenclature if necessary.

B) Explain why 3-menthene (rather than 2.8. EXPLAIN WHY menthyl chloride gives only 2-menthene as its E2 elimination product. (12 pts) Consider the following E2 elimination reactions of menthyl chloride and neomenthyl chloride: A) Using mechanistic reasoning. 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) .menthene) is the major product in the E2 elimination of neomenthyl chloride.

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). (12 pts) Bromoetherification. only draw one of the two structures. Clearly indicate stereochemistry where appropriate.9. Br2 O Br + HBr HO 10. the addition of the elements Br and OR to a double bond. is a common method for constructing rings containing oxygen atoms. a) H2SO4 OH heat Br2 CH3 b) CCl4 CH2CH3 H2 c) Pt CH2CH3 . If the major product is a pair of enantiomers. 4 each) Give the structure of the major organic product of each of the following reactions. conc. Draw a stepwise mechanism for the following INTRAMOLECULAR bromoetherification reaction. (28 pts.

NaOH H2O O Cl H O O g) CH2Cl2 .d) H3C CH2CH3 1) O3 H CH2CH3 2) CH3SCH3 3) H30+ e) OsO4 H2O2 CH3 1) BH3.THF f) 2) H2O2.