1. Predict the product for the following reaction.

OH O
H3CO OCH3

OH H OH

II III
I

HO OCH3 O

H OCH3

IV V
I
II
III
IV
V
Ans: B

2. Which of the following compounds is least reactive towards nucleophilic addition

reaction?
O O

O O

H H

H H

I II III IV
A) I
B) II
C) III
D) IV
E) Both I & IV
Ans: A
3. Predict the product for the following reaction.

O O
O O
H
H

I O II O
O
III
O O

H
H
H H
IV V
O
I
II
III
IV
V
Ans: E

4. Predict the product for the following reaction.

PCC
3-methyl-1-octanol
CH2Cl2
A) 3-methyloctanone
B) 3-methyloctanal
C) 2-methyloctanone
D) 2-methyloctanal
E) 2-methyloctanoic acid
Ans: B
 5. Predict the product for the following reaction.

OH OH

OH
O O
O O

III IV V
I II
A) I
B) II
C) III
D) IV
E) V
Ans: A

6. Provide the reactant(s) necessary to prepare the following compound.

N

NH2 H2SO4
7. Predict the product(s) for the following reaction

O
H3O+

O O OH
OH OH O
HO HO HO
H
+ + +

I II III
O
O
OH
OH
H
HO HO

+ +

IV V
I
II
III
IV
V
A

8. Predict the product(s) for the following reaction

O
H3O+
O
D

Ans: O

HO OH
 9. Provide the reagents necessary to carry out the following conversion.
O

Br

1. Mg/ether
O

2. H
3. H3O+
4. PCC/CH2Cl2

10. Which of the following is the IUPAC name for the following compound?

A. 1-methyl-2-cyclohexene
B. 2-methylcyclohexene
C. 3-methylcyclohexene
D. 1-methyl-5-cyclohexene
Ans: C

11. Viridenomycin, shown below, is a polyene antibiotic that displays anti-tumor activity. Its
structural complexity and chemical instability have made it a challenging target for
organic chemists to synthesize. Ignoring the benzene ring, how many disubstituted Z
alkenes are present in viridenomycin?

A. 1
B. 2
C. 3
D. 4
Ans: C
 12. Which one of the following compounds is the strongest acid?

A) I
B) II
C) III
D) IV
E) V
Ans: E

13. Predict the product for the following reaction.

I
II
III
IV
none of these
Ans: D
 14. Which of the following reactions would not yield isopropyl acetate as major
product?

A&C
Ans: B

15. The expected major product of the following reaction is:

HBr
?

Br
A)
Br

B)
Br
C)
Br
D)
Br

Br
E)
Ans: C

16. The reaction shown below would be expected to produce as major products which of the
following compounds?
HCl
 + enantiomer
A) Cl

+ enantiomer
B) Cl

Cl + enantiomer
C)
Cl
+ enantiomer
D)

+ enantiomer
Cl
E)
Ans: D

17. Which of the following is the major product of the reaction shown?

A) I
B) II
C) III
D) IV
Ans: D

18. Which reaction intermediate is formed when 4-methylcyclohexene reacts with Br2 dissolved
in CCl4?
Br Br Br
Br
H 3C H 3C H3C Br Br

I II III IV V
A) I
B) II
C) III
D) IV
 E) V
Ans: B

19. What is the expected major product for the following reaction?

Br2, CH3OH
?

OH Br OCH3
H3CO
H3CO
Br Br OCH3 Br Br
+ + + +
enantiomer enantiomer enantiomer enantiomer

I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D

20. Treatment of 1,2-dimethylcyclopentene with OsO4, followed by aqueous NaHSO3, produces

which of the following:
OH OH OH CH3 CH3
CH3 CH3 CH3 H H
CH3 OH H OH H
OH CH3 CH3 CH3 CH3
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: A

21. Which reagents are most likely to accomplish the transformation shown below?

? OH

A) 1. BH3·THF / 2. HO–, H2O2, H2O

 B) H+ , H2 O
C) 1. Hg(OAc)2, H2O, THF / 2. NaBH4
D) 1. Hg(OAc)2, CH3OH / 2. NaBH4
E) NaOH, H2O
Ans: A

22. What are the expected major products of the reaction sequence shown below?

1. O3
?
2. H2O

O O
O O C O O
HO
OH

I II III IV V

A) I and II
B) I, III, and V
C) II, III, and IV
D) I and IV
E) II, III, IV
Ans: D

23. Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH4
followed by water?
O O
O

H
I II III
O O

H
IV V
I
II
III
IV
V
Ans: A

24. Draw the detailed step by step mechanism for an alkene hydration using
the mercuriation/demercuriation methodology
(see slideshow for the answer)

25. Draw the detailed step by step mechanism for the acid-catalyzed
hydrolysis of an acetal.

(see slideshow for the answer)