Name: __________________________ Date: _____________
1. Which would be the product of the following reaction sequence?
O i) SOCl2
?
OH ii) benzene, AlCl3
iii) Zn(Hg), HCl
SO2 CO2 CH2
I II III
IV V
A) I
B) II
C) III
D) IV
E) V
2. Cl
The reaction of benzene with in the presence of anhydrous aluminum
chloride produces principally which of these?
II III
I
IV V
A) I
B) II
C) III
D) IV
E) V
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3. Which compound is an acetal?
O
O
OH
O OH O OCH3 O
I II III IV
A) I
B) II
C) III
D) IV
E) All of the above
4. Consider the following reaction: what is the expected product?
NH2
Br2, H2O ?
Cl
NH2 Cl
Br Br Br Br Br Br
H2N Cl
Cl NH2
I II III
NH2 NH2
Br Br
Br
Cl Cl
IV V
A) I
B) II
C) III
D) IV
E) V
5. What is the correct structure for 2,3-dimethyl-2-hepten-4-one?
O
O O
I II
III
IV O
V
A) I
B) II
C) III
D) IV
E) V
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6. Which is the best sequence of reactions for the following transformation?
O
NO 2
A) i) HNO3, H2SO4; ii) CH3MgBr, Et2O; iii) H3O+, heat
B) i) CH3MgBr, Et2O; ii) H3O+, heat; iii) HNO3, H2SO4
C) i) HNO3, H2SO4; ii) NaBH4, H2O; iii) H3O+, heat
D) i)HNO3, H2SO4; ii) LiAlH4, H2O; iii) H3O+, heat
E) None of these syntheses is satisfactory.
7. What is the major product of the following reaction sequence?
OCH3 i) OH, HCl
HO
?
O ii) LAH, Et2O
O
iii) H2O, H3O+
OH O OH
O
HO HO O
I II III
OH OH
O
O
IV V
A) I
B) II
C) III
D) IV
E) V
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8. The product, K, of the following sequence of reactions would be:
MgBr
AlCl3 H3 O+
I J K
ether heat
Cl
(-H2O)
O
O
HO
III
I II
OH
V
IV
A) I
B) II
C) III
D) IV
E) V
9. Which of the reactions listed below would serve as a synthesis of acetophenone,
O
C6H5CCH3 ?
OH
A)
PCC
CH2Cl2
B) AlCl3
C6H6 + CH3COCl
C) ether H 3O +
C6H5CN + CH3Li
D) Answers A) and B) only
E) Answers A), B), and C)
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10. Which sequence of reactions would be utilized to convert
CH3
O CO2CH3 into O C CH3 ?
OH
A) 2CH3MgBr, then NH4+
B) HOCH2CH2OH, H3O+; LiAlH4, ether; 2CH3MgBr, then NH4+
C) HOCH2CH2OH, H3O+; 2CH3MgBr, then NH4+
D) HOCH2CH2OH, H3O+; H2, Pt; CH3OH, NH4+
E) None of the above
11. How might the following synthesis be carried out:
several
steps
Cl
A) CH3CH2Cl Cl2
C6H6 product
AlCl3 FeCl3
B) Cl2 CH3CH2Cl
C6H6 product
FeCl3 AlCl3
C) O
CH3CCl Cl2 Zn(Hg)
C6H6 product
AlCl3 FeCl3 HCl
D) O
CH3CCl Zn(Hg) Cl2
C6H6 product
AlCl3 HCl FeCl3
E) None of these syntheses is satisfactory.
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12. In which of the following reactions is the final product expected to be formed as a
racemic mixture?
A) H
C6H5MgBr + C6H5C O
B) O
HCN + CH3CCH3
O
C)
H
+ HCN
D) H
CH3C O + xs CH3OH + HCl (xs=excess)
E) O
CH3CHCH2COC2H5 + (i-Bu)2AlH
CH3
13. What would you expect to be the major product obtained from the following reaction?
O
Br2, FeBr3
O
?
O O
O
Br
O O
O
Br
Br
I II III
Br
O O
O Br O
IV V
A) I
B) II
C) III
D) IV
E) V
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14. What would you expect to be the major product obtained from the following reaction?
Cl2
?
light
Cl
Cl
Cl
I II III
Cl
Cl
IV V
A) I
B) II
C) III
D) IV
E) V
15. What is the major product of the following reaction sequence?
HCN H2SO4
O
H2O
heat
CN H
NOSO3H COH CN OSO3H CNH2
O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
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Answer Key
1. C
2. A
3. B
4. B
5. E
6. A
7. E
8. D
9. E
10. C
11. D C is correct answer (Not D)
12. C
13. D
14. E
15. B
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