Unlock document.
This document is partially blurred.
Unlock all pages and 1 million more documents.
Get Access
Chapter 12 Testbank (Klein)- Draft 3
Chapter 12
Topic: One-Step Syntheses
Section: 12.1
Difficulty Level: Easy
1. Predict the major product(s) for the following reaction:
HBr
Br
Br
I II
Br
III
Br
IV
A) I
B) II
C) III
D) IV
E) I and III
2. Provide the reagent(s) required to complete the following transformation:
Br
??
A) HBr
B) Br2/h
C) Br2/ROOR
D) HBr/ROOR
E) h /NBS
3. Provide the reagent(s) required to complete the following transformation:
??
Br
A) HBr
B) Br2/h
C) Br2/ROOR
D) HBr/ROOR
E) h /NBS
4. Provide the reagent(s) required to complete the following transformation:
?? Br
Br
+ En
A) HBr
B) Br2/h
C) Br2
D) HBr/ROOR
E) h /NBS
5. Provide the reagent(s) required to complete the following transformation:
Br
OH
+ En
??
A) HBr
B) Br2/H2O
C) Br2
D) HBr/ROOR
E) h /NBS
6. Provide the reagent(s) required to complete the following transformation:
OH
??
A) NaOH
B) heat/H2SO4
C) CH3CO2H
D) NaOEt
E) KOtBu
7. Predict the major product(s) for the following transformation:
Br
NaSH
SH
Br HS HS
I II III IV
A) I
B) II
C) III
D) IV
E) I and III
Chapter 12
8. Predict the reagent(s) required to complete the following transformation:
Br ??
A) NaOtBu
B) HBr
C) H2SO4
D) NaOH
E) NaSH
9. Predict the reagent(s) required to complete the following transformation:
Br ??
A) NaOtBu
B) HBr
C) H2SO4
D) NaOH
E) NaSH
10. Predict the major product(s) obtained from the following reaction:
Cl
DBU
DBU
III III IV
A) I
B) II
C) III
D) IV
E) II and IV
11. Predict the reagent(s) required to complete the following transformation:
OH
OH + En
??
A) 1) OsO4; 2) NaHSO3, H2O
B) 1) Hg(OAc)2, H2O; 2) NaBH4
C) 1) RCO3H; 2) H3O+
D) H2SO4, H2O
E) 1) O3; 2) DMS
12. Predict the reagent(s) required to complete the following transformation:
OH
OH
+ En
??
A) 1) OsO4; 2) NaHSO3, H2O
B) 1) Hg(OAc)2, H2O; 2) NaBH4
C) 1) RCO3H; 2) H3O+
D) H2SO4, H2O
E) 1) O3; 2) DMS
13. Predict the reagent(s) required to complete the following transformation:
??
H
O O
A) 1) OsO4; 2) NaHSO3, H2O
B) 1) Hg(OAc)2, H2O; 2) NaBH4
C) 1) RCO3H; 2) H3O+
D) H2SO4, H2O
E) 1) O3; 2) DMS
14. Predict the reagent(s) required to complete the following transformation:
OH + En
??
A) 1) OsO4; 2) NaHSO3, H2O
B) 1) Hg(OAc)2, H2O; 2) NaBH4
C) 1) RCO3H; 2) H3O+
D) 1) BH3-THF; 2) H2O2, NaOH
E) 1) O3; 2) DMS
15. Predict the reagent(s) required to complete the following transformation:
+ En
??
OH
A) 1) OsO4; 2) NaHSO3, H2O
B) 1) Hg(OAc)2, H2O; 2) NaBH4
C) 1) RCO3H; 2) H3O+
D) 1) BH3-THF; 2) H2O2, NaOH
E) 1) O3; 2) DMS
16. Predict the reagent(s) required to complete the following transformation:
??
+ En
A) 1) OsO4; 2) NaHSO3, H2O
B) 1) Hg(OAc)2, H2O; 2) NaBH4
C) H2, Pt
D) 1) BH3-THF; 2) H2O2, NaOH
E) 1) O3; 2) DMS
Chapter 12
17. Predict the reagent(s) required to complete the following transformation:
??
A) 1) OsO4; 2) NaHSO3, H2O
B) NaNH2
C) H2, Pt
D) Na, NH3(l)
E) H2, Lindlar’s catalyst
18. Predict the reagent(s) required to complete the following transformation:
??
A) 1) OsO4; 2) NaHSO3, H2O
B) NaNH2
C) H2, Pt
D) Na, NH3(l)
E) H2, Lindlar’s catalyst
19. Predict the reagent(s) required to complete the following transformation:
??
H
O
A) 1) OsO4; 2) NaHSO3, H2O
B) 1) Hg(OAc)2, H2O; 2) NaBH4
C) H2, Pt
D) 1) 9-BBN; 2) H2O2, NaOH
E) 1) O3; 2) DMS
20. Predict the reagent(s) required to complete the following transformation:
??
O
A) 1) OsO4; 2) NaHSO3, H2O
B) H2SO4, H2O, HgSO4
C) H2, Pt
D) 1) 9-BBN; 2) H2O2, NaOH
E) 1) O3; 2) DMS
Difficulty Level: Easy
21. Predict the reagent(s) required to complete the following transformation:
Br Br
?? Na
A) 1) OsO4; 2) NaHSO3, H2O
B) H2SO4, H2O, HgSO4
C) NaOH
D) xs NaNH2
E) 1) O3; 2) DMS
22. Predict the reagent(s) required to complete the following transformation:
??
O
OH
+ CO2
A) 1) OsO4; 2) NaHSO3, H2O
B) H2SO4, H2O, HgSO4
C) NaOH
D) xs NaNH2
E) 1) O3; 2) H2O
23. Predict the reagent(s) required to complete the following transformation:
??
n
A) 1) OsO4; 2) NaHSO3, H2O
B) ROOR, heat
C) NaOH
D) xs NaNH2
E) 1) O3; 2) H2O
24. Predict the reagent(s) required to complete the following transformation:
??
Br
A) 1) OsO4; 2) NaHSO3, H2O
B) HBr, ROOR
C) NaBr
D) xs NaNH2
E) HBr
25. Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5-
dimethylhex-1-yne.
A) 1) OsO4; 2) NaHSO3, H2O
B) HBr, ROOR
C) NaBr
D) 1) xs NaNH2; 2) H3O+
E) HBr
26. Predict the reagent(s) required to convert 1-bromo-1-methylcyclohexane to 1-
bromo-2-methylcyclohexane.
A) 1) KOtBu; 2) HBr
B) 1) NaOEt; 2) HBr
C) 1) NaOEt; 2) HBr, ROOR
D) 1) KOtBu; 2) HBr, ROOR
E) Br2, h
27. Which of the following sequences of reagents will move the alcohol functional
group from the tertiary position of 1-methyl-1-cyclohexanol to a secondary
position?
A) 1) KOtBu; 2) Hg(OAc)2, H2O; 3) NaBH4
B) 1) TsCl, pyr; 2) KOtBu; 3) BH3-THF; 4) H2O2, NaOH
C) 1) H2SO4, heat; 2) BH3-THF; 3) H2O2, NaOH
D) 1) TsCl, pyr; 2) NaOH; 3) BH3-THF; 4) H2O2, NaOH
E) C and D will both work
F) A and B will both work
28. Which sequence of reagents will accomplish the following transformation?
Br
?? Br
A) 1) KOtBu; 2) HBr
B) 1) NaOEt; 2) HBr, ROOR
C) 1) H2SO4, heat; 2) Br2, h
D) 1) NaOEt; 2) HBr
E) both A and D work
29. Which sequence of reagents will accomplish the following transformation?
??
A) 1) KOtBu; 2) 1-bromopropane
B) 1) NaNH2; 2) 1-bromopropane
C) 1) NaNH2; 2) 2-bromopropane
D) 1) O3; 2) DMS
E) 1) O3; 2) 1-bromopropane
30. Predict the major product(s) for the following reaction:
1) NaNH2
2) CH3I
??
III III IV
A) I
B) II
C) III
D) IV
E) II and III
31. Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium
amide followed by reaction with bromoethane.
A) Hept-1-en-4-yne
B) Hept-6-en-3-yne
C) Hept-3-en-6-yne
D) Hept-4-en-1-yne
32. Reaction of compound A (molecular formula = C7H12) with sodium amide
followed by reaction with 1-bromobutane produces
(CH3)2CHCH(CH3)CC(CH2)3CH3. What is the name of compound A?
A) 2,3-dimethylnon-4-yne
B) 2,2-dimethylpent-1-yne
C) 3,4-dimethylpent-1-yne
D) 4,4-dimethylhept-1-yne
E) 1-heptyne
33. Reaction of compound A (molecular formula = C12H22) with ozone followed by
reaction with DMS produces only (CH3)3CCH2CHO. Which of the following
could be compound A?
A) cis-2,3,7,8-tetramethyloct-4-ene
B) trans-dodec-6-ene
C) 4,4-dimethylpent-1-ene
D) cis-2,2,7,7-tetramethyloct-4-ene
E) 2,2-dimethyldec-4-ene
34. Predict the reagent(s) required to complete the following reaction:
O
HO
O
OH
??
A) NaNH2
B) 1) O3; 2) H2O
C) KMnO4
D) 1) BH3-THF; 2) H2O2, NaOH
E) H2SO4, H2O
35. Compound X has molecular formula C8H10. Reaction of Compound X with
excess ozone, followed by reaction with dimethyl sulfide and finally rinsing with
water produces only the compounds shown below. Draw a possibility for
Compound X that is consistent with these results.
O
O
H
HO O
+OH
O
Compound X 1) O3
2) DMS
3) H2O
(C8H10)H
36. Predict the products of the following reaction:
1) O3
2) DMS
3) H2O
H H
O
O
C
OHC OH COOH
O
O O
OHC CHO
O
III III IV VVI
A) I, III, and IV
B) II, III, and IV
C) I, III, and V
D) II, IV, and VI
E) III and IV
37. One compound is produced when acetylene is treated with the following reagents.
What is the IUPAC name of this compound?
1) NaNH2
2) 1-bromopropane
3) NaNH2
4) 1-bromopropane
5) ozone
6) water
??
38. Predict a correct sequence of reactants required to complete the following
transformation in which propanal is the only carbon-containing product.
H
O
??
NaNH2
S
H2OBr O3Na/NH3(l) H2/Pt
III III IV VVI VII
A) 1) I; 2) III; 3) IV; 4) V; 5) II
B) 1) VI; 2) IV; 3) IV; 4) VII; 5) V; 6) II
C) 1) V; 2) II
D) 1) I; 2) IV; 3) VI; 4) V; 5) II
E) none of the above are correct
39. Propose an efficient synthesis of propanoic acid from acetylene:
40. Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:
O
??
