Chapter 10
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Klein, Organic Chemistry 1e
Section: 10.2
1. What is the correct IUPAC name for the following structure?
a. 3,9-dimethyl-3-decyne
b. 3,9-dimethyl-7-decyne
c. 2,8-dimethyl-7-decyne
d. 2,8-dimethyl-3-decyne
Klein, Organic Chemistry 1e
Answer: d.
For more examples of this type of problem, see Skillbuilder
10.1.
Klein, Organic Chemistry 1e
Section: 10.3
2. Which bases are strong enough to deprotonate the following
compound efficiently?
Klein, Organic Chemistry 1e
Answer: A, D, E.
For more examples of this type of problem, see Skillbuilder
10.2.
Klein, Organic Chemistry 1e
Alternate Answers:
Section: 10.3
2. Which bases are strong enough to deprotonate the following
compound efficiently?
A. A, B, C
B. A, B, D
C. A, B, E
D. A, D, E
E. A, D, F
Klein, Organic Chemistry 1e
Answer: d
Klein, Organic Chemistry 1e
Section: 10.4
3. Which of the following structures will form alkynes upon treatment
with NaNH2?
A. D.
Br
Br Br Br
B. E.
Br
Br Br
C. Br F. Br
Br
Br
Klein, Organic Chemistry 1e
Answer: A. B, C, D, F.
Klein, Organic Chemistry 1e
Alternate Answer:
Section: 10.4
3. Which of the following structures will form alkynes upon treatment
with NaNH2?
A. D.
Br
Br Br Br
B. E.
Br
Br Br
C. Br F. Br
Br
Br
A. A, B, C, D, E, F
B. A, B, C, D, E
C. A, B, C, D, F
D. A, B, D, E, F
E. A, C, D, E, F
Klein, Organic Chemistry 1e
Answer: c
Klein, Organic Chemistry 1e
Section: 10.5
4. What reagent is needed for the following reaction?
a. H2/Lindlar's Catalyst
b. 1) Na in NH3 2) NH4Cl
c. H2/Pt
d. H2/Ni2B
e. a and d
f. none of the above
Klein, Organic Chemistry 1e
Answer: b.
The product is a trans double bond.1) Na in NH3 2) NH4Cl is the
only way to turn an alkyne into a trans double bond.
Klein, Organic Chemistry 1e
Alternate Answer:
Section: 10.5
4. What reagent is needed for the following reaction?
a. H2/Lindlar's Catalyst
b. 1) Na in NH3 2) NH4Cl
c. H2/Pt
d. H2/Ni2B
e. a and d
Klein, Organic Chemistry 1e
Answer: b.
Klein, Organic Chemistry 1e
Section: 10.5
5. What reagent is needed for the following reaction?
a. H2/Lindlar's Catalyst
b. 1) Na in NH3 2) NH4Cl
c. H2/Pt
d. H2/Ni2B
e. a and d
f. none of the above
Klein, Organic Chemistry 1e
Answer: e.
The product is a cis double bond. H2/Lindlar's Catalyst and
H2/Ni2B can both be used to turn an alkyne into a cis double
bond.
Klein, Organic Chemistry 1e
Alternate Answer:
Section: 10.5
5. What reagent is needed for the following reaction?
a. H2/Lindlar's Catalyst
b. 1) Na in NH3 2) NH4Cl
c. H2/Pt
d. H2/Ni2B
e. a and d
Klein, Organic Chemistry 1e
Answer: e.
Klein, Organic Chemistry 1e
Section: 10.6
6. Which reaction scheme can be used to produce this halide?.
Br
A. HBr C. HBr
1 equivalent 2 equivalents
HBr, H2O2 HBr, H2O2
B. D.
1 equivalent 2 equivalents
Klein, Organic Chemistry 1e
Answer: a
Klein, Organic Chemistry 1e
Section: 10.7
7. Which reactions give ketones? Which reactions give aldehydes?
I. Ketones
II. Aldehydes
Klein, Organic Chemistry 1e
Answer: I: A, C, D, F
II: B, E
For more examples of this type of problem, see Skillbuilder
10.4.
Klein, Organic Chemistry 1e
Alternate Answer:
Section: 10.7
7. Which reactions give ketones? Which reactions give aldehydes?
A. I = C, D, E, F; II = A, B
B. I = B, D, E, F; II = A, C
C. I = B, C, D, F; II = A, E
D. I = A, D, E, F; II = B, C
E. I = A, C, D, F; II = B, E
Klein, Organic Chemistry 1e
Answer: e
Klein, Organic Chemistry 1e
Section: 10.8
8. What are the product(s) of this reaction?
Klein, Organic Chemistry 1e
Answer: b.
Klein, Organic Chemistry 1e
Alternate Answer:
Section: 10.8
8. What are the product(s) of this reaction?
A. A
B. B
C. C
D. B and E
E. D and F
Klein, Organic Chemistry 1e
Answer: b.
Klein, Organic Chemistry 1e
Section: 10.9
9. What are the product(s) of this reaction?
1) O3
2) H2O
O O
A. C.
OH OH
B. OH
D. O C O
O
Klein, Organic Chemistry 1e
Answer: a, d.
Klein, Organic Chemistry 1e
Alternate Answers:
Section: 10.9
9. What are the product(s) of this reaction?
1) O3
2) H2O
O O
A. C.
OH OH
B. OH
D. O C O
O
A. A
B. B
C. C
D. A and D
E. B and C
Klein, Organic Chemistry 1e
Answer: D.
Klein, Organic Chemistry 1e
Section: 10.10
10. What is the product of the following reaction?
1) NaNH2
NaCl + NH3 + ????
2) Pentyl chloride
A. C.
B. D.
Klein, Organic Chemistry 1e
Answer: b
For more examples of this type of problem, see Skillbuilder
10.5.
Klein, Organic Chemistry 1e
Section: 10.11
11. What is the correct order of reagents needed for the following
transformation?
a. xs. NaNH2
b. NaNH2
c. NaOMe
d. H3O+
e. Propyl Chloride
f. Butyl Chloride
g. Pentyl chloride
Klein, Organic Chemistry 1e
Answer: a, f.
For more examples of this type of problem, see Skillbuilder
10.6.
Klein, Organic Chemistry 1e
Alternate Answers:
Section: 10.11
11. What is the correct order of reagents needed for the following
transformation?
a. xs. NaNH2
b. NaNH2
c. NaOMe
d. H3O+
e. Propyl Chloride
f. Butyl Chloride
g.Pentyl chloride
A. A, E
B. A, F
C. A, G
D. B, F
E. B, G
Klein, Organic Chemistry 1e
Answer: b
Klein, Organic Chemistry 1e
Section: 10.11
12. What is the correct order of reagents needed for the
following transformation?
Br
Br
a. xs NaNH2
b. NaOMe
c. H2/Lindlar's Catalyst
d. Na/NH3
e. H2/Pt
f. Propyl Chloride
g. Butyl Chloride
h. Pentyl chloride
Klein, Organic Chemistry 1e
Answer: a, g, e.
The starting material has 5 carbons and the product has 9
carbons. Therefore, you need to add four carbons to get the
product, which means you need butyl chloride. The final
product has an alkane so only H2/Pt will produce the alkane.
For more examples of this type of problem, see Skillbuilder
10.6.
Klein, Organic Chemistry 1e
Alternate Answers:
Section: 10.11
12. What is the correct order of reagents needed for the
following transformation?
Br
Br
a. xs NaNH2
b. NaOMe
c. H2/Lindlar's Catalyst
d. Na/NH3
e. H2/Pt
f. Propyl Chloride
g. Butyl Chloride
h.Pentyl chloride
A. A, F, C
B. A, F, E
C. A, G, C
D. A, G, E
E. A, H, C Klein, Organic Chemistry 1e
Answer: d
Klein, Organic Chemistry 1e
Section: 10.11
13. What is the correct order of reagents needed for the
following transformation?
a. HBr/CCl4
b. NaOMe
c. Potassium tert-butoxide
d. 1) O3 2) H2O
e. HBr/H2O2
Klein, Organic Chemistry 1e
Answer: e, c, d.
First an anti-Markovnikov addition of HBr to the alkene places a
Bromine on the second carbon. Next, elimination using
potassium tert-butoxide gives the Hofmann product, a terminal
alkene. Finally, oxidative cleavage gives CO2 and the 5 carbon
carboxylic acid, 2-methylbutanoic acid. For more examples of
this type of problem, see Skillbuilder 10.6.
Klein, Organic Chemistry 1e
Alternate Answers:
Section: 10.11
13. What is the correct order of reagents needed for the
following transformation?
a. HBr/CCl4
b. NaOMe
c. Potassium tert-butoxide
d. 1) O3 2) H2O
e. HBr/H2O2
A. A, B, D
B. A, C, D
C. E, B, D
D. E, C, D
Klein, Organic Chemistry 1e
Answer: d
Klein, Organic Chemistry 1e
