1.

Chlorination of pentane gives a mixture of isomers having the molecular formula

C5H11Cl. The percentage of 1-chloropentane is 22%. Assuming the secondary
hydrogens in pentane are equally reactive to monochlorination, what is the percentage
of 3-chloropentane in the mixture?
A. 48%
B. 26%
C. 22%
D. 14%

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Bloom's Level: 3. Apply
Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

2. Which one of the following gives a single monochlorination product?

A. 2,2-dimethylpropane
B. 2,3-dimethylbutane
C. 2,2-dimethylbutane
D. 2-methylpropane

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Bloom's Level: 3. Apply
Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

3. Which of the following hydrocarbons has the slowest reaction rate with Br 2 and light?

A. CH4
B. CH3CH2CH3
C. CH3CH2CH2CH3
D. (CH3)3CH

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Bloom's Level: 4. Analyze
Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Subtopic: Radical stability
Topic: Radical Reactions

10-1
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4.How many monochlorination products do you expect in the following reaction?

A. two
B. three
C. four
D. five

Bloom's Level: 3. Apply

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10-2
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5.Which of the following is the most stable radical?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.01
Subtopic: Radical stability
Topic: Radical Reactions

10-3
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6.Which of the following are the chain propagating steps in the free radical chlorination of
methane?

A. I and III
B. II and VI
C. III and IV
D. III and V

Bloom's Level: 2. Understand

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.03
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10-4
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 °
7.Calculate ΔH of reaction for the free radical bromination of cyclopentane to give
bromocyclopentane.

A. -121 kJ/mol
B. -63 kJ/mol
C. +121 kJ/mol
D. +63 kJ/mol

Bloom's Level: 3. Apply

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.01
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

8. Which constitutional isomer of C 6H14 gives only two monochlorination products?

A. 2-methylpentane
B. 2,2-dimethylbutane
C. 3-methylpentane
D. 2,3-dimethylbutane

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Bloom's Level: 3. Apply
Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10-5
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McGraw-Hill Education.
9.Consider the following reaction (X = Cl or Br).

Which statement(s) is(are) correct?

I. Statistically the 1-halopropane should be the major isomer.

II. The 2-halopropane to 1-halopropane ratio is largest when X=Br.

III. The 2-halopropane to 1-halopropane ratio is the largest when X=Cl.

A. only II
B. only III
C. I and II
D. I and III

Bloom's Level: 2. Understand

Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10. Studies indicate that the methyl radical is trigonal planar. Based on this, which of
the following best describes the methyl radical?

2 2
A. The carbon is sp hybridized and the unpaired electron occupies an sp orbital.
2
B. The carbon is sp hybridized and the unpaired electron occupies a 2p orbital.
3 3
C. The carbon is sp hybridized and the unpaired electron occupies an sp orbital.
3
D. The carbon is sp hybridized and the unpaired electron occupies a 2p orbital.

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Bloom's Level: 2. Understand
Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.01
Subtopic: Radical stability
Topic: Radical Reactions

10-6
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McGraw-Hill Education.
11. Dibromination of isopropylcyclopentane gives a product that can be isolated in good
yields. Which of the following would you predict to be this product?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply

Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10-7
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12. Which of the following is the key intermediate in the chlorination reaction below?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 10
Difficulty: Easy
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

13. How many C3H6Cl2 constitutional isomers do you expect in the dichlorination

of propane?
A. two
B. three
C. four
D. five

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Bloom's Level: 3. Apply
Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10-8
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14. Upon free-radical chlorination, the alkane shown would yield

A. a single monochloride.
B. three isomeric monochlorides.
C. two isomeric dichlorides.
D. four isomeric monochlorides.

Bloom's Level: 3. Apply

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

15. What is the major product in the monochlorination of pentane?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10-9
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16.The reaction shown below is what type?

A. addition
B. termination
C. propagation
D. initiation

Bloom's Level: 2. Understand

Chapter: 10
Difficulty: Easy
Gradable: automatic
Section: 10.03
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

17.If you wanted to get the best yield of compound B from compound A, you would:

A. use chlorine + light rather than bromine + light

B. use bromine + light rather than chlorine + light
C. neither would give >50% yield
D. either would give >50% yield

Bloom's Level: 5. Evaluate

Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10-10
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18.Where would this reaction occur fastest in this molecule?

A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Subtopic: Radical stability
Topic: Radical Reactions

10-11
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19.Which species below is the intermediate in the free radical addition of HBr to 1-butene?

A. A
B. B
C. C
D. D

Bloom's Level: 2. Understand

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.05
Subtopic: Radical addition to alkenes and alkynes
Topic: Radical Reactions

10-12
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20.Which of the following does not give 1-bromo-1-methylcyclopentane as the major
product?

A. A
B. B
C. C
D. D

Bloom's Level: 3. Apply

Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.05
Subtopic: Radical addition to alkenes and alkynes
Topic: Radical Reactions

10-13
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21.What reagents would be required to accomplish the conversion shown below?

A. NaOCH3, then Br2 and light.

B.KOCH3, then HBr and peroxides.

C. NaOCH3, then HBr.
t
D. KO Bu, then Br2 and light.

Bloom's Level: 4. Analyze

Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.07
Subtopic: Radical addition to alkenes and alkynes
Topic: Radical Reactions

10-14
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McGraw-Hill Education.
22.Which reaction below gives a single enantiomer of a chiral product?

A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze

Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.05
Subtopic: Chiral vs achiral molecules
Subtopic: Radical addition to alkenes and alkynes
Subtopic: Stereoisomers (enantiomers, diastereomers, meso)
Topic: Radical Reactions
Topic: Stereochemistry

10-15
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McGraw-Hill Education.
23.Which statement would be true of this reaction?

A. The organic product is achiral.

B. The product is racemic.
C. The product is more of one enantiomer than the other.
D. There is no way to guess the stereochemistry.

Bloom's Level: 2. Understand

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.04
Subtopic: Chiral vs achiral molecules
Subtopic: Halogenation of alkanes
Subtopic: Stereoisomers (enantiomers, diastereomers, meso)
Topic: Radical Reactions
Topic: Stereochemistry

24.What is the major product of the reaction sequence shown below?

A. 2-methyl-1-butene
B.2-methyl-2-butene
C.3-methyl-1-butene
D. 2-methylbutane

Bloom's Level: 3. Apply

Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.04
Subtopic: Halogenation of alkanes
Topic: Radical Reactions

10-16
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25. Which reagent below would be used to convert 2-pentyne to trans-2-pentene?

A. NaNH2, NH3
B. Na, NH3
C. H2, Lindlar Pd
D. H2O, HgSO4/H2SO4

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Bloom's Level: 2. Understand
Chapter: 10
Difficulty: Easy
Gradable: automatic
Section: 10.06
Subtopic: Radical addition to alkenes and alkynes
Topic: Radical Reactions

26.Which of the following is the correct IUPAC name of the product for the reaction shown
below?

A. cis-2-methyl-5-heptene
B. cis-6-methyl-2-heptene
C. trans-2-methyl-5-heptene
D. trans-6-methyl-2-heptene

Bloom's Level: 3. Apply

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.06
Subtopic: Radical addition to alkenes and alkynes
Topic: Radical Reactions

27. When alkynes are treated with sodium metal, Na, in liquid ammonia, sodium acts as a

A. Brønsted acid.
B. Brønsted base.
C. reducing agent.
D. catalyst.

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Bloom's Level: 2. Understand
Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.06
Subtopic: Radical addition to alkenes and alkynes
Topic: Radical Reactions

10-17
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28.How would you carry out the following conversion?

A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze

Chapter: 10
Difficulty: Hard
Gradable: automatic
Section: 10.07
Subtopic: Radical addition to alkenes and alkynes
Topic: Radical Reactions

10-18
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29.It is believed that the trans alkenyl radical, shown below, is an intermediate in the sodium
metal reduction of an alkyne. Based on this information, the unpaired electron would be
located in which of the following orbitals?

A. sp
2
B. sp
3
C. sp
D. 2p

Bloom's Level: 2. Understand

Chapter: 10
Difficulty: Medium
Gradable: automatic
Section: 10.06
Subtopic: Radical addition to alkenes and alkynes
Subtopic: Radical stability
Topic: Radical Reactions

30. Which halogen forms the weakest bond to carbon?

A. F
B. Cl
C. Br
D. I

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Bloom's Level: 2. Understand
Chapter: 10
Difficulty: Easy
Gradable: automatic
Section: 10.01
Subtopic: Radical stability
Topic: Radical Reactions

10-19
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McGraw-Hill Education.
 Category # of Questions
Accessibility: Keyboard Navigation 9
Bloom's Level: 2. Understand 12
Bloom's Level: 3. Apply 12
Bloom's Level: 4. Analyze 5
Bloom's Level: 5. Evaluate 1
Chapter: 10 30
Difficulty: Easy 4
Difficulty: Hard 9
Difficulty: Medium 17
Gradable: automatic 30
Section: 10.01 4
Section: 10.03 2
Section: 10.04 15
Section: 10.05 3
Section: 10.06 4
Section: 10.07 2
Subtopic: Chiral vs achiral molecules 2
Subtopic: Halogenation of alkanes 18
Subtopic: Radical addition to alkenes and alkynes 9
Subtopic: Radical stability 6
Subtopic: Stereoisomers (enantiomers, diastereomers, meso) 2
Topic: Radical Reactions 30
Topic: Stereochemistry 2

10-20
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McGraw-Hill Education.