BR BR BR BR

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
Br Br
III IV
I II
A) I
B) II
C) III
D) IV
E) I and III
Ans: E
Chapter 12
Section: 12.1
2. Provide the reagent(s) required to complete the following transformation:
Br
??
A) HBr

B) Br 2/h!
C) Br 2/ROOR
D) HBr/ROOR
E) h! /NBS
Ans: D
Chapter 12
Section: 12.1
Br
??
A) HBr
B) Br 2/h!
C) Br 2/ROOR
D) HBr/ROOR
E) h! /NBS
Ans: E
Chapter 12
Section: 12.1
Br
??
Br
+ En
A) HBr

B) Br 2/h!
C) Br 2
D) HBr/ROOR
E) h! /NBS
Ans: C
Chapter 12
Section: 12.1
OH
??
+ En
Br

A) HBr
B) Br 2/H2O
C) Br 2
D) HBr/ROOR
E) h! /NBS
Ans: B
Chapter 12
Section: 12.1
OH
??

A) NaOH
B) heat/H2SO4
C) CH3CO2H
D) NaOEt
E) KOtBu
Ans: B
Chapter 12
Section: 12.1
7. Predict the major product(s) for the following transformation:
NaSH
Br

SH
Br HS HS
I II III IV

A) I
B) II
C) III
D) IV
E) I and III
Ans: C
Chapter 12


Section: 12.1
8. Predict the reagent(s) required to complete the following transformation:
??
Br
A) NaOt Bu
B) HBr
C) H2SO4
D) NaOH
E) NaSH
Ans: D
Chapter 12
Section: 12.1
??
Br
A) NaOt Bu
B) HBr
C) H2SO4
D) NaOH
E) NaSH
Ans: A

Chapter 12
Section: 12.1
10. Predict the major product(s) obtained from the following reaction:
Cl
DBU
DBU
I II III IV

A) I
B) II
C) III
D) IV
E) II and IV
Ans: C
Chapter 12
Section: 12.1

??
OH
+ En
OH

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
Ans: C
Chapter 12
Section: 12.1
??
+ En
OH
OH


C)
+
1) RCO3H; 2) H3O
D) H2SO4, H2O
E) 1) O3; 2) DMS
Ans: A
Chapter 12
Section: 12.1

O O
??

C) 1) RCO3H; 2) H3O+
D) H2SO4, H2O
E) 1) O3; 2) DMS
Ans: E
Chapter 12
Section: 12.1
??
OH
+ En

C) 1) RCO3H; 2) H3O+
D) 1) BH3-THF; 2) H2O2, NaOH
E) 1) O3; 2) DMS
Ans: B
Chapter 12

Section: 12.1
??
+ En
OH


C)
+
1) RCO3H; 2) H3O
E) 1) O3; 2) DMS
Ans: D
Chapter 12
Section: 12.1
??
+ En

C) H2, Pt
E) 1) O3; 2) DMS
Ans: C
Chapter 12


Section: 12.1
??

B) NaNH2
C) H2, Pt
D) Na, NH3(l)
E) H2, Lindlar’s catalyst
Ans: D
Chapter 12
Section: 12.1
??

B) NaNH2
C) H2, Pt
D) Na, NH3(l)
E) H2, Lindlar’s catalyst
Ans: E
Chapter 12

Section: 12.1
??
H


C) H2, Pt
D) 1) 9-BBN; 2) H2O2, NaOH
E) 1) O3; 2) DMS
Ans: D
Chapter 12
Section: 12.1
??

B) H2SO4, H2O, HgSO4
C) H2, Pt
D) 1) 9-BBN; 2) H2O2, NaOH
E) 1) O3; 2) DMS
Ans: B
Chapter 12
Section: 12.1

Na
??
Br Br

C) NaOH
D) xs NaNH2
E) 1) O3; 2) DMS
Ans: D
Chapter 12
Section: 12.1
O
??
+ CO2
OH

C) NaOH
D) xs NaNH2
E) 1) O3; 2) H2O
Ans: E
Chapter 12

Section: 12.1
??

B) ROOR, heat
C) NaOH
D) xs NaNH2
E) 1) O3; 2) H2O
Ans: B
Chapter 12
Section: 12.1
Br
??

B) HBr, ROOR
C) NaBr
D) xs NaNH2
E) HBr

Ans: E
Chapter 12
Topic: Functional Group Transformations
Section: 12.2
25. Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5-

dimethylhex-1-yne.

B) HBr, ROOR
C) NaBr
D)
+
1) xs NaNH2; 2) H3O
E) HBr
Ans: D
Chapter 12
Section: 12.2
Difficulty Level: Medium
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) Br 2, h!
Ans: C
Chapter 12
Section: 12.2
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
Ans: E
Chapter 12
Section: 12.2
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) Br 2, h!
D) 1) NaOEt; 2) HBr
E) both A and D work
Ans: E
Chapter 12
Topic: Reactions that Change the Carbon Skeleton
Section: 12.3
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
Ans: B
Chapter 12
Section: 12.3
30. Predict the major product(s) for the following reaction:
1) NaNH2
??
2) CH3I
I II III IV
A) I
B) II
C) III
D) IV
E) II and III
Ans: C
Chapter 12
Section: 12.3
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
Ans: A
Chapter 12
Section: 12.3
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
Ans: C
Chapter 12
Section: 12.3
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
Ans: D
Chapter 12
Section: 12.3
34. Predict the reagent(s) required to complete the following reaction:

?? HO
OH
O

A) NaNH2
B) 1) O3; 2) H2O
C) KMnO4
E) H2SO4, H2O
Ans: B
Chapter 12
Section: 12.3
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
Compound X 1) O3
+
OH
(C8H10)
2) DMS H O
3) H2O HO O
Ans:
Chapter 12
Section: 12.3
36. Predict the products of the following reaction:

1) O3
2) DMS
3) H2O
O O O O
O
C
H H O OHC OH COOH OHC CHO
II III IV VI
I V
A) I, III, and IV

B) II, III, and IV
C) I, III, and V
D) II, IV, and VI
E) III and IV
Ans: B
Chapter 12
Section: 12.3
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

Ans: butanoic acid
Chapter 12
Section: 12.3
38. Predict a correct sequence of reactants required to complete the following

transformation in which propanal is the only carbon-containing product.

?? O
S
NaNH2 H2O O3 Na/NH3(l) H2/Pt
Br
I II III IV V VI 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
Ans: D
Chapter 12
Section: 12.3
39. Propose an efficient synthesis of propanoic acid from acetylene:
1) NaNH2 1) O3
CO2H
2) CH3CH2Br 2) H2O
Ans:
Chapter 12
Topic: How to Approach a Synthesis Problem
Section: 12.4
40. Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:
??
O

O
Br
Br2, h! KOtBu 1) ozone
2) DMS
Ans:
Chapter 12
Section: 12.4
41. Identify the changes that must occur in transforming cis-2-butene into 2-butanol:
A) only the identity of the functional group(s) must change

B) only the carbon skeleton must change
C) only the location of the functional group(s) must change
D) only the identity and location of the functional group(s) must change
E) both the carbon skeleton and the identity of the functional group(s)
must change
Ans: A
Chapter 12
Section: 12.4
42. Propose an efficient synthesis of 1-butene from propyne:
1) NaNH2 1) NaNH2
2) MeI 2) H2O
3) H2/Lindlar
Ans:
Chapter 12
Section: 12.4
43. The following sequence of reactions transforms acetylene into a compound with
an altered carbon skeleton (compound 1), and from that into a compound in which
the functional group has been changed (compound 2). Identify compounds 1 and
2:

1) NaNH2
1) H2, Ni2B
1 2
2) bromoethane
2) BH3-THF
3) H2O2, NaOH
OH
OH
I II III IV
OH
OH
V VI VII VIII
A) Compound 1 = I; Compound 2 = III

B) Compound 1 = II; Compound 2 = III
C) Compound 1 = VI; Compound 2 = IV
D) Compound 1 = II; Compound 2 = IV
E) Compound 1 = II; Compound 2 = V
F) Compound 1 = VII; Compound 2 = VIII
Ans: D
Chapter 12
Section: 12.4
44. Which of the following sequences efficiently converts 2-methylpropene and

sodium acetylide into 3-methylbutanal?
??
3-methylbutanal
A) 1) HBr; 2) NaCCH; 3) O3; 4) H2O

B) 1) HBr; 2) NaCCH; 3) O3; 4) DMS
C) 1) HBr, ROOR; 2) NaCCH; 3) O3; 4) H2O
D) 1) HBr, ROOR; 2) NaCCH; 3) H2/Ni2B 3) O3; 4) DMS
E) 1) NaCCH; 2) H2/Ni2B; 3) O3; 4) DMS
Ans: D
Chapter 12

Section: 12.4
45. Which of the following sequences most efficiently converts 3-methyl-1-pentene

into 3-bromo-3-methylpentane?
A) 1) HBr; 2) NaOH; 3) HBr

B) 1) Br 2, h!; 2) H2, Pt
C) 1) H2, Pt; 2) Br 2, h!
D) 1) NBS, h!; 2) H2, Pt
E) 1) HBr, ROOR; 2) NaOH; 3) HBr
Ans: C
Chapter 12
Section: 12.4
Difficulty Level: Difficult
46. Propose a strategy to carry out the following transformation:
O
??
OH
1) NBS, h!
2) H2, Pt
3) NaCCH
4) xs O3
5) H2O
Ans:
Chapter 12
Section: 12.4
47. Propose an efficient method of converting 3-methyl-2-butanol into 3-methyl-1-

butanol.

OH
1) TsCl, pyr
2) KOtBu
3) BH3-THF
4) H2O2, NaOH
Ans: OH
Chapter 12
Section: 12.4
48. Propose an efficient method of converting 3-methyl-1-butanol into 3-methyl-2-

butanol.
OH
1) H2SO4, heat
2) Hg(OAc)2, H2O
3) NaBH4
OH
Ans:
Chapter 12
Section: 12.4
49. Which of the following alkenes cannot be converted into an alkyne by reaction
with bromine followed by excess sodium amide and then with water?
I II III IV
A) I
B) II
C) III
D) IV
E) III and IV
Ans: D

Chapter 12
Section: 12.4
50. Which of the following provides an efficient method of converting 3-bromo-2-

methyl-1-butene into 2-methyl-2-butene?
A) 1) NaOH; 2) H2, Pt

B) 1) H2, Pt; 2) NaOEt
C) 1) H2, Pt; 2) xs NaNH2
D) 1) H2, Ni2B; 2) KOtBu
E) 1) H2, Pt; 2) KOtBu
Ans: B
Chapter 12
Section: 12.4
51. Which order of alterations would most effectively transform trans-2-butene into
1-butene?
A) convert to the dibromoalkane, then to the terminal alkyne, then to the
terminal alkene
B) convert to an alcohol, then to a terminal alkyne, finally to the terminal
alkene
C) convert to the terminal alkene in one step
D) shorten the chain by two carbons, then add a two-carbon alkene to the
end
E) convert to an alkane, then to a terminal alkyne, and finally to a terminal
alkene
Ans: A
Chapter 12
Section: 12.4
52. What is the minimum number of steps required to convert 2-methylpropane into
2-methylpropene?
A) 1
B) 2

C) 3
D) 4
E) 5
Ans: B
Chapter 12
Section: 12.4
53. What is the minimum number of steps required to convert 2-methylpropane into
1-bromo-2-methyl-2-propanol?
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: C
Chapter 12
Section: 12.4
54. Propose an efficient method of completing the following transformation:
??
OH
+ En
Br
HO

1) NaCCCH3
2) Na/NH3(l)
3) OsO4
4) NaHSO3, H2O
Ans: Br
Chapter 12

Section: 12.4
??
1) 1 Br2, h!
2) KOtBu
3) HBr, ROOR
4) NaSMe
Ans:
Chapter 12
Section: 12.4
S
Br
??
S
Br
1) NaOEt
2) NBS, h!
3) NaSMe
Ans:
Chapter 12
Section: 12.4

O
??
OH
O
1) Br2
2) xs NaNH2
3) H2O OH
4) O3
5) H2O
Ans:
Chapter 12
Section: 12.4
Br
??
CHO
Br 1) NaCCH
2) 9-BBN
CHO
3) H2O2, NaOH
Ans:
Chapter 12
Topic: Retrosynthetic Analysis
Section: 12.5
59. Demonstrate your understanding of retrosynthetic synthesis and determine which

compound(s) could lead immediately to the alkene shown below:

??
Br
I II III IV

A) I
B) II
C) III
D) IV
E) I and IV
F) I, III, and IV
Ans: E
Chapter 12
Section: 12.5
60. Using retrosynthetic synthesis, determine which compound(s) could lead

immediately to the alcohol shown below:
OH
??
I II III IV

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

Chapter 12
Section: 12.5
61. Using retrosynthetic synthesis, determine which compound(s) could lead

immediately to the alkyne shown below:
??
Br Br
Br Br Br
I II III IV

A) I
B) II
C) III
D) IV
E) I and II
F) I, II, and IV
Ans: D
Chapter 12
Section: 12.5
62. Using the concept of retrosynthetic synthesis, determine which compound(s)

could lead immediately to the alkane shown below:
??
Br OH
I II III IV

A) II and III
B) I and IV
C) I
D) II
E) III
F) IV
Ans: B
Chapter 12
Section: 12.5
63. Using the concept of retrosynthetic synthesis, determine which compound(s)

could lead immediately to the bromoalkene shown below:
Br ??
OH
Br Br
I II III IV
A) I and III

B) I and IV
C) I
D) II
E) III
F) IV
Ans: C
Chapter 12
Section: 12.5
64. Show that you understand the concept of retrosynthetic analysis by working
backwards two steps in the synthesis below. Identify possible combinations of A
and B that could lead to the alkyl halide (C):

B A
Br
C
Br
I II III IV
Br
OH
Cl
VI VII VIII
V
A) B = I and A = VI
B) B = VI and A = I
C) B = III and A = VII
D) B = IV and A = VII
E) B = I and A = III
F) B = V and A = VIII
Ans: A, D, and E
Chapter 12
Section: 12.5
and B that can lead to the alkyne (C):

B A
Br
Br
Br
I II III IV
Br
OH
Cl
Br
VI VII VIII
V
A) B = I and A = VI
B) B = VI and A = I
F) B = VI and A = VIII
Ans: B
Chapter 12
Section: 12.5
and B that can lead to the alcohol (C):

OH
B A
Br
Br
Br
I II III IV
Br Br
Cl
Br
VI VII VIII
V
A) B = I and A = VI
B) B = VI and A = I
F) B = VIII and A = V
Ans: D and F
Chapter 12
Section: 12.5
and B that can lead to the compound shown (C):

B A
OH
+ En
OH
OH
Br
Br
I II III IV
Cl
VI VII VIII
V
A) B = I and A = VI
B) B = VI and A = I
C) B = V and A = II
F) B = VIII and A = V
Ans: C
Chapter 12
Section: 12.5
and B that can lead to the alkene (C):

B A
Br HO
I II III
Br
V VI VII
A) B = I and A = V
B) B = II and A = VII
C) B = III and A = I
D) B = I and A = VII
E) B = II and A = VI
F) B = III and A = II
Ans: B and E
Chapter 12
Section: 12.5
69. Devise a method of converting methylcyclobutane into cyclopentene.

??
1) Br2, h!
2) KOtBu
3) BH3-THF
Ans:
4) H2O2, NaOH
5) H2SO4, heat

Chapter 12
Section: 12.5
70. Devise a method of converting ethylene into PVC (polyvinyl chloride).
1) Br2
2) xs NaNH2
3) H2O
n
4) 1 eq HCl
Cl
5) ROOR, heat
Ans:
Chapter 12
Section: 12.5
71. Devise a method of converting acetylene into the polymer shown below.
Cl
1) NaNH2
2) CH3Br
3) HCl
Ans:
4) ROOR, heat

Chapter 12
Section: 12.5
72. Devise a method of converting trans-2-methyl-3-hexene into 5-methylhexanal.
1) Br2
2) xs NaNH2
3) H2O
CHO
4) disiamylborane
5) H2O2, NaOH
Ans:
Chapter 12
Section: 12.5
73. Devise a method of converting trans-2-methyl-3-hexene into 4-methylpentanoic

acid.
1) Br2
2) xs NaNH2
3) H2O
COOH
4) ozone
5) H2O
Ans:
Chapter 12
Section: 12.5
74. Which of the following effectively produces 4,4-dimethyl-2-pentyne?

+ NaCCCH3
A)
Br
B) + CH3Br
+ 2 NaNH2
C)
Br Br
+ 1 NaNH2
D)
Br
Ans: B and C
Chapter 12
Section: 12.5
75. Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-
tetramethyl-2-ethylcyclohexane.

OH
+ En
OH
1) Br2, h!
2) KOtBu
3) HBr, ROOR
Ans: 4) KOtBu
5) Br2
6) xs NaNH2
7) CH3Br
8) H2, Lindlar
9) OsO4
10) NaHSO3, H2O

Chapter 12
Section: 12.5
76. Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-
tetramethyl-2-ethylcyclohexane.

OH
+ En
OH
1) Br2, h!
2) KOtBu
3) HBr, ROOR
Ans: 4) KOtBu
5) Br2
6) xs NaNH2
7) CH3Br
8) H2, Lindlar
9) RCO3H
10) H3O+
Chapter 12
Section: 12.5
77. Devise an efficient synthesis of the compound shown below starting with 4-
methyl-2-pentanol.
OH
1) TsCl, pyr
OH 2) KOtBu
3) HBr/ROOR
4) O
Ans:
ONa
Chapter 12


Section: 12.5
78. To add one carbon directly to the end of a primary alkyl bromide, one could:
A) substitute bromide with acetylide, then cleave the triple bond.
B) substitute bromide with acetylide, then reduce the alkyne to an alkene.
C) substitute bromide with methoxide.
D) eliminate hydrogen bromide to produce an alkene.
Ans: A
Chapter 12
Section: 12.5
79. To remove one carbon from the end of a primary alkyl bromide, one could:
A) substitute bromide with acetylide, then cleave the triple bond.
B) substitute bromide with acetylide, then reduce the alkyne to an alkene.
C) substitute bromide with methoxide.
D) eliminate hydrogen bromide to produce an alkene, then cleave the
double bond.
Ans: D
Chapter 12
Section: 12.5
80. Devise a method to complete the following synthesis.

??
Br +
OH OH
1) NaOEt
2) BH3-THF
Br +
Ans:
3) H2O2, NaOH
OH OH
Chapter 12
Section: 12.5
acetylene
1) NaNH2
2) CH3Br
3) NaNH2
4) CH3Br
Ans:
5) H2, Lindlar's catalyst

6) RCO3H

Chapter 12
Section: 12.5

+ En acetylene
1) NaNH2
2) CH3Br
3) NaNH2
4) CH3Br
Ans:
5) Na, NH3(l)
6) RCO3H

Chapter 12
Section: 12.5
N N
1) NBS, h!
2) HBr, ROOR
Ans: N N
3) 2 NaCN
Chapter 12
Section: 12.5
84. Devise a method to prepare 1,7-heptanediol from propene.
1) NBS, h!
2) HBr, ROOR
Ans:
3) 2 NaCCH HO OH
4) H2, Lindlar
5) BH3-THF
6) H2O2, NaOH

Chapter 12
Section: 12.5
85. Devise a method to prepare 1,3-dibromopropanol from propene.
1) NBS, h!

2) Br2, H2O Br Br
Ans:
OH
Chapter 12
Section: 12.5
86. Devise a method to prepare 3-bromo-1-propanol from propene.
1) NBS, h!

2) BH3-THF Br OH
Ans:
3) H2O2, NaOH

Chapter 12
Section: 12.5

1) NBS, h!
2) KCN
Ans:
N
Chapter 12
Section: 12.5
88. Devise a synthesis to lengthen the legs of “Ralph” as requested below.

1) NBS, h!
2) HBr, ROOR
3) 2 NaCCH
4) H2, Pt
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Chapter 12 Testbank (Klein)- Draft 3

1. Predict the major product(s) for the following reaction:

2. Provide the reagent(s) required to complete the following transformation:

3. Provide the reagent(s) required to complete the following transformation:

4. Provide the reagent(s) required to complete the following transformation:

5. Provide the reagent(s) required to complete the following transformation:

6. Provide the reagent(s) required to complete the following transformation:

7. Predict the major product(s) for the following transformation:

Topic: One-Step Syntheses

8. Predict the reagent(s) required to complete the following transformation:

9. Predict the reagent(s) required to complete the following transformation:

11. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

12. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

Difficulty Level: Easy

13. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

14. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

15. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

16. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

Topic: One-Step Syntheses

17. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

18. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

19. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

20. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

Difficulty Level: Easy

21. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

22. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

23. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

24. Predict the reagent(s) required to complete the following transformation:

A) 1) OsO4; 2) NaHSO3, H2O

25. Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5-

A) 1) OsO4; 2) NaHSO3, H2O

26. Predict the reagent(s) required to convert 1-bromo-1-methylcyclohexane to 1-

A) 1) KOtBu; 2) HBr

A) 1) KOtBu; 2) Hg(OAc)2, H2O; 3) NaBH4

C) 1) H2SO4, heat; 2) BH3-THF; 3) H2O2, NaOH

28. Which sequence of reagents will accomplish the following transformation?

A) 1) KOtBu; 2) HBr

29. Which sequence of reagents will accomplish the following transformation?

30. Predict the major product(s) for the following reaction:

32. Reaction of compound A (molecular formula = C7H12) with sodium amide

33. Reaction of compound A (molecular formula = C12H22) with ozone followed by

34. Predict the reagent(s) required to complete the following reaction:

35. Compound X has molecular formula C8H10. Reaction of Compound X with

36. Predict the products of the following reaction:

H H O OHC OH COOH OHC CHO