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Predict The Product For The Following Reaction.: I II III
Predict The Product For The Following Reaction.: I II III
OH O
H3CO OCH3
OH H OH
II III
I
HO OCH3 O
H OCH3
IV V
I
II
III
IV
V
Ans: B
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
OH OH
OH
O O
O O
III IV V
I II
A) I
B) II
C) III
D) IV
E) V
Ans: A
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
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
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
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
21. Which reagents are most likely to accomplish the transformation shown below?
? OH
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.