Chapter 12

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Klein, Organic Chemistry 1e

Section: 12.1 and 12.2

1. Identify the reagents necessary to accomplish each of the

transformations shown below. If more than one reagent is needed, list
all reagents. OH
O
OH

A B C

Br
H D Br

G E
F
OH
Br
Br
Br
+ enantiomer

1 = HBr 9 = 1) BH3.THF 2) H2O2, NaOH

2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = 1) MCPBA 2) H3O+
4 = Br2, H2O 12 = OsO4 (catalytic), NMO
5 = Br2, CH3OH 13 = 1) O3 2) DMS
6 = TsCl, pyridine 14 = NaOMe
7 = 1) Hg(OAc)2, H2O 2) NaBH4 15 = KOC(CH3)3 Klein, Organic Chemistry 1e
Answer: A: 7
B: 8
C: 9
D: 2
E: 4
F: 10
G: 3
H: 1

Klein, Organic Chemistry 1e

ALTERNATE Question and Answer:
 
1. Identify the reagents necessary to accomplish
transformations shown below. If more than one reagent is
needed, list all reagents.
1 = HBr 9 = 1) BH3.THF 2) H2O2, NaOH
OH
O 2 = HBr, HOOH 10 = H2/Pt
OH 3 = Br2 11 = 1) MCPBA 2) H3O+
4 = Br2, H2O 12 = OsO4 (catalytic), NMO
5 = Br2, CH3OH 13 = 1) O3 2) DMS
A B C
6 = TsCl, pyridine 14 = NaOMe
7 = 1) Hg(OAc)2, H2O 2) NaBH4 15 = KOC(CH3)3
Br 8 = 1) Hg(OAc)2, EtOH 2) NaBH4 16 = NBS, hn
H D Br  
A.7, 5, 9, 1, 4, 10, 3, 2
B.9, 8, 7, 1, 4, 10, 3, 2
G E C.7, 8, 9, 1, 4, 10, 3, 2
F D.7, 8, 9, 2, 4, 10, 3, 1
E.9, 8, 7, 2, 5, 10, 3, 1
OH
Br
Br
Br
+ enantiomer

Klein, Organic Chemistry 1e

Answer: D.

For more examples of this type of problem, see Skillbuilder

12.1.

Klein, Organic Chemistry 1e

Section: 12.1 and 12.2
2. Identify the reagents necessary to accomplish each of the transformations
shown below. If more than one reagent is needed, list all reagents. B, F and H
will produce a pair of enantiomers and only one is shown (Also make note of
the direction of the arrow in transformations A and D).

  
1 = HBr 9 = 1) BH3.THF 2) H2O2, NaOH
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = 1) MCPBA 2) H3O+
4 = Br2, H2O 12 = OsO4 (catalytic), NMO
5 = Br2, CH3OH 13 = 1) O3 2) DMS
6 = TsCl, pyridine 14 = NaOMe
7 = 1) Hg(OAc)2, H2O 2) NaBH4 15 = KOC(CH3)3
8 = 1) Hg(OAc)2, EtOH 2) NaBH4 16 = NBS, hn Klein, Organic Chemistry 1e
Answer: A: 6, 14
B: 11
C: 13
D: 14
E: 5
F: 12
G: 16
H: 9
 
For more examples of this type of problem, see Skillbuilder
12.1.

Klein, Organic Chemistry 1e

ALTERNATE Question and Answer:

2. Identify the reagents necessary to accomplish transformations shown below.

If more than one reagent is needed, they will be listed inside parentheses,
separated by commas. B, F and H will produce a pair of enantiomers and only
one is shown (Also make note of the direction of the arrow in transformations A
and D).

  
1 = HBr 9 = 1) BH3.THF 2) H2O2, NaOH
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = 1) MCPBA 2) H3O+
4 = Br2, H2O 12 = OsO4 (catalytic), NMO
5 = Br2, CH3OH 13 = 1) O3 2) DMS
6 = TsCl, pyridine 14 = NaOMe
7 = 1) Hg(OAc)2, H2O 2) NaBH4 15 = KOC(CH3)3
8 = 1) Hg(OAc)2, EtOH 2) NaBH4 16 = NBS, hn

A.14, 12, 13, 14, 5, 11, 16, 7

B.15, 11, 13, 15, 5, 12, 3, 9
C.(6, 14), 11, 13, 14, 5, 12, 16, 9
D.(6, 14), 12, 13, 14, 5, 11, 16, 9
E.(6, 14), 11, 13, 15, 5, 12, 3, 7 Klein, Organic Chemistry 1e
Answer: C
 
For more examples of this type of problem, see Skillbuilder
12.1.

Klein, Organic Chemistry 1e

 Section: 12.2
 
3. Propose a plausible synthesis for the following transformation.

1 = HBr 9 = 1) BH3.THF 2) H2O2, NaOH

2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = 1) MCPBA 2) H3O+
4 = Br2, H2O 12 = OsO4 (catalytic), NMO
5 = Br2, CH3OH 13 = 1) O3 2) DMS
6 = TsCl, pyridine 14 = NaOMe
7 = 1) Hg(OAc)2, H2O 2) NaBH4 15 = KOC(CH3)3
8 = 1) Hg(OAc)2, EtOH 2) NaBH4 16 = 1) xs NaNH2/NH3 2) H2O

Klein, Organic Chemistry 1e

Answer: 6, 14, 2, 15, 11
 
For more examples of this type of problem, see Skillbuilder
12.1 and 12.2.

Klein, Organic Chemistry 1e

 Alternate Answers:

Section: 12.2
 
3. Propose a plausible synthesis for the following transformation.

1 = HBr 9 = 1) BH3.THF 2) H2O2, NaOH

2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = 1) MCPBA 2) H3O+
4 = Br2, H2O 12 = OsO4 (catalytic), NMO
5 = Br2, CH3OH 13 = 1) O3 2) DMS
6 = TsCl, pyridine 14 = NaOMe
7 = 1) Hg(OAc)2, H2O 2) NaBH4 15 = KOC(CH3)3
8 = 1) Hg(OAc)2, EtOH 2) NaBH4 16 = 1) xs NaNH2/NH3 2) H2O

A.14, 2, 15, 11
B.14, 2, 15, 12
C.6, 14, 2, 15, 12
D.6, 14, 1, 15, 11 Klein, Organic Chemistry 1e
Answer: E
 
For more examples of this type of problem, see Skillbuilder
12.1.

Klein, Organic Chemistry 1e

 Section: 12.2
 
4. Propose a synthetic route for the following transformation.

1 = HBr 9 = 1) BH3.THF 2) H2O2, NaOH

2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = 1) MCPBA 2) H3O+
4 = Br2, H2O 12 = OsO4 (catalytic), NMO
5 = Br2, CH3OH 13 = 1) O3 2) DMS
6 = TsCl, pyridine 14 = NaOMe
7 = 1) Hg(OAc)2, H2O 2) NaBH4 15 = KOC(CH3)3
8 = 1) Hg(OAc)2, EtOH 2) NaBH4 16 = 1) xs NaNH2/NH3 2) H2O

Klein, Organic Chemistry 1e

Answer: 2, 15, 3, 16
 
For more examples of this type of problem, see Skillbuilder
12.1 and 12.2.

Klein, Organic Chemistry 1e

 Alternate Answers:

Section: 12.2
 
4. Propose a synthetic route for the following transformation

1 = HBr 9 = 1) BH3.THF 2) H2O2, NaOH

2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = 1) MCPBA 2) H3O+
4 = Br2, H2O 12 = OsO4 (catalytic), NMO
5 = Br2, CH3OH 13 = 1) O3 2) DMS
6 = TsCl, pyridine 14 = NaOMe
7 = 1) Hg(OAc)2, H2O 2) NaBH4 15 = KOC(CH3)3
8 = 1) Hg(OAc)2, EtOH 2) NaBH4 16 = 1) xs NaNH2/NH3 2) H2O

•1, 15, 3, 14
•2, 14, 4, 15
•9, 6, 14, 3, 15
•9, 6, 15, 2, 16
•2, 15, 3, 16 Klein, Organic Chemistry 1e
Answer: E
 
For more examples of this type of problem, see Skillbuilder
12.1 and 12.2.

Klein, Organic Chemistry 1e

Section: 12.1, 12.2, 12.3 and 12.4
 
5. Propose the shortest synthetic route for the following transformation.

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

Klein, Organic Chemistry 1e

Answer: 3, 9, 7, 13
 
Answer: Response: For more examples of this type of problem,
see Skillbuilder 12.1, 12.2, 12.3 and 12.4.

Klein, Organic Chemistry 1e

Alternate Answer:

Section: 12.1, 12.2, 12.3 and 12.4

 
5. Propose the shortest synthetic route for the following transformation.

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

A.3, 9, 7, 13
B.3, 9, 7, 12
C.3, 16, 7, 12 Klein, Organic Chemistry 1e
D.3, 16, 7, 13
Answer: A
 
For more examples of this type of problem, see Skillbuilder
12.1 12.2 and 12.3.

Klein, Organic Chemistry 1e

Section:12.1, 12.2, 12.3 and 12.4
 
6. Propose the shortest synthetic route for the following transformation.

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

Klein, Organic Chemistry 1e

Answer: 3, 9, 5, 12

For more examples of this type of problem, see Skillbuilder

12.1, 12.2, 12.3 and 12.4.

Klein, Organic Chemistry 1e

Alternate Answers:

 Section: 12.1, 12.2, 12.3 and 12.4

 
6. Propose the shortest synthetic route for the following transformation.

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

A. A, B, C, C
B. A, B, D, C
C. B, A, C, D
Klein, Organic Chemistry 1e
D. B, D, A, C
Answer: E
 
For more examples of this type of problem, see Skillbuilder
12.1 12.2 and 12.3.

Klein, Organic Chemistry 1e

Section: 12.1, 12.2, 12.3 and 12.4
 
7. Propose the shortest synthetic route for the following transformation.

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

Klein, Organic Chemistry 1e

Answer: 3, 9, 8, 10 or 3, 9
 
For more examples of this type of problem, see Skillbuilder
12.1, 12.2, 12.3 and 12.4.

Klein, Organic Chemistry 1e

Alternate Answer:

Section: 12.1, 12.2, 12.3 and 12.4

 
7. Propose the shortest synthetic route for the following transformation.

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

A.3, 9, 8, 10
B.3, 9, 8, 11
C.3, 9, 8, 12
D.3, 9, 9, 13 Klein, Organic Chemistry 1e
Answer: A
 
For more examples of this type of problem, see Skillbuilder
12.1 12.2 and 12.3.

Klein, Organic Chemistry 1e

Section: 12.1, 12.2, 12.3 and 12.4
 
8. Propose the shortest synthetic route for the following transformation.

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

Klein, Organic Chemistry 1e

Answer: 2, 16, 3, 9, 7, 10
 
For more examples of this type of problem, see Skillbuilder
12.1, 12.2, 12.3 and 12.4.

Klein, Organic Chemistry 1e

Alternate Answer:

Section: 12.1, 12.2, 12.3 and 12.4

 
8. Propose the shortest synthetic route for the following transformation.

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

A.3, 9, 7, 10
B.3, 16, 3, 9, 7, 10
C.3, 16, 3, 9, 8, 10
D.2, 16, 3, 9, 7, 10 Klein, Organic Chemistry 1e
Answer: D
 
For more examples of this type of problem, see Skillbuilder
12.1 12.2 and 12.3.
 

Klein, Organic Chemistry 1e

Section: 12.1, 12.2, 12.3 and 12.4
 
9. Propose the shortest synthetic route for the following
transformation. O O
+
OH HO

  
1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

Klein, Organic Chemistry 1e

Answer: 3, 9, 7, 14
 
For more examples of this type of problem, see Skillbuilder
12.1, 12.2, 12.3 and 12.4.
 

Klein, Organic Chemistry 1e

Alternate Answer:

Section: 12.1, 12.2, 12.3 and 12.4

 
9. Propose the shortest synthetic route for the following transformation.
O O
+
OH HO

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2
4 = CH3Cl 12 = H2/Lindlar’s Catalyst
5 = CH3CH2Cl 13 = Na/NH3
6 = CH3CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2Cl 16 = KOC(CH3)3

A.3, 9, 7, 14
B.3, 9, 7, 15
C.3, 9, 8, 14
D.3, 9, 8, 15 Klein, Organic Chemistry 1e
Answer: A
 
For more examples of this type of problem, see Skillbuilder
12.1 12.2 and 12.3.
 
 

Klein, Organic Chemistry 1e

 Section: 12.5
 
10. Propose the shortest synthetic route for the following
transformation (5-dodecanone will also be produced in your synthetic
route).

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2/Wilkinson’s Catalyst
4 = H2SO4 12 = H2/Lindlar’s Catalyst
5 = H2SO4, H2O, HgSO4 13 = Na/NH3
6 = CH3CH2CH2CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2CH2CH2Cl

Klein, Organic Chemistry 1e

Answer: 3, 9, 7, 5
 
For more examples of this type of problem, see Skillbuilder
12.1, 12.2, 12.3 and 12.4.

Klein, Organic Chemistry 1e

Alternate Answers:

Section: 12.5
 
10. Propose the shortest synthetic route for the following
transformation (5-dodecanone will also be produced in your
synthetic route).?

1 = HBr 9 = xs NaNH2/NH3
2 = HBr, HOOH 10 = H2/Pt
3 = Br2 11 = H2/Wilkinson’s Catalyst
4 = H2SO4 12 = H2/Lindlar’s Catalyst
5 = H2SO4, H2O, HgSO4 13 = Na/NH3
6 = CH3CH2CH2CH2CH2Cl 14 = 1) O3 2) H2O
7 = CH3CH2CH2CH2CH2CH2Cl 15 = 1) O3 2) DMS
8 = CH3CH2CH2CH2CH2CH2CH2Cl
A. 3, 9, 6, 4
B. 3, 9, 6, 10, 5
C. 3, 9, 7, 10, 4
D. 3, 9, 7, 10, 5
Klein, Organic Chemistry 1e
E. 3, 9, 7, 5
Answer: E
 
For more examples of this type of problem, see Skillbuilder
12.1 12.2 and 12.3.

Klein, Organic Chemistry 1e