Chapter 11

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Klein, Organic Chemistry 1e

Section: 11.1

1. Radicals are formed through  ___ .

a. Heterolysis
 b. Homolysis
 c. Ozonolysis

Klein, Organic Chemistry 1e

Answer: b.
 

Klein, Organic Chemistry 1e

Section: 11.1

2. What is the geometry of alkyl radicals?

 a. tetrahedral
 b. linear
 c. trigonal planar
 d. trigonal pyrimidal

Klein, Organic Chemistry 1e

Answer: c.

Klein, Organic Chemistry 1e

Section: 11.1

3. What is the general order of radical stability (from most stable

to least stable)?

 a. methyl > primary > secondary > tertiary

 b. primary > secondary > tertiary > methyl

 c. tertiary > secondary > primary > methyl

 d. tertiary > primary > secondary > methyl

Klein, Organic Chemistry 1e

Answer: c.

Klein, Organic Chemistry 1e

 Section: 11.1

4. Which fishhook arrows will generate the resonance structure

shown below?

A. C.

B. D.

Klein, Organic Chemistry 1e

Answer: d.

For more examples of this type of problem, see Skillbuilder

11.1.

Klein, Organic Chemistry 1e

 Section: 11.1

5. Rank the indicated carbon-hydrogen bonds from the

STRONGEST to the WEAKEST.

Klein, Organic Chemistry 1e

Answer: D, A, B, E, C.

For more examples of this type of problem, see Skillbuilder

11.2.

Klein, Organic Chemistry 1e

 Alternate Answers:

Section: 11.1

5. Rank the indicated carbon-hydrogen bonds from the

STRONGEST to the WEAKEST.

A. A, B, D, E, C
B. B, A, D, E, C
C. C, E, B, A, D
D. D, A, B, E, C
E. E, D, A, C, B

Klein, Organic Chemistry 1e

Answer: d

Klein, Organic Chemistry 1e

Section: 11.2

6.  ___  and  ___  can be used to form radicals.

 a. Light and high temperatures

 b. Light and cool temperatures

 c. Dark and high temperatures

 d. Dark and cool temperatures

Klein, Organic Chemistry 1e

Answer: a

Klein, Organic Chemistry 1e

 Section: 11.3

7. List in order the mechanistic steps for the following reaction.

Klein, Organic Chemistry 1e

Answer: C, A D, B.

For more examples of this type of problem, see Skillbuilder

11.3 and 11.4.

Klein, Organic Chemistry 1e

Alternate Answers:

 Section: 11.3

7. List in order the mechanistic steps for the following reaction.

A. A, B, C, C
B. A, B, D, C
C. B, A, C, D
D. B, D, A, C
E. C, A, D, B 

Klein, Organic Chemistry 1e

Answer: e

Klein, Organic Chemistry 1e

Section: 11.3

8. Identify each of the mechanistic steps below

I. Initiation
II. Propagation
III. Termination

Klein, Organic Chemistry 1e

Answer: A: I
B: II
C. II
D. III

For more examples of this type of problem, see Skillbuilder

11.3 and 11.4.

Klein, Organic Chemistry 1e

Alternate Answer:

Section: 11.3
8. Identify each of the mechanistic steps below

I. Initiation
II. Propagation
III. Termination

A. A = I; B = I; C = II; D = III
B. A = I; B = II; C = II; D = III
C. A = I; B = II; C = III; D = III
D. A = I; B = II; C = I; D = III
E. A = II; B = I; C = II; D = III

Klein, Organic Chemistry 1e

Answer: b.

Klein, Organic Chemistry 1e

Section: 11.3

9. Which of the following bonds would be most susceptible to

radical formation?

 a. carbon carbon single bond

 b. oxygen oxygen single bond

 c. hydrogen hydrogen single bond

 d. oxygen hydrogen single bond

 e. carbon hydrogen single bond

Klein, Organic Chemistry 1e

Answer: b.
 

Klein, Organic Chemistry 1e

Section: 11.5

10. Radical halogenation reactions using  ___  are the most

 ___  and often lead to multiple products. While radical
halogenation reactions using  ___  are the most  ___  and
produce primarily the major product.

 a. bromine, selective, chlorine, reactive

 b. bromine, reactive, chlorine, selective

 c. chlorine, selective, bromine, reactive

 d. chlorine, reactive, bromine, selective

Klein, Organic Chemistry 1e

Answer: d.

Chlorine is the more reactive halogen and bromine is the more

selective.

Klein, Organic Chemistry 1e

Section: 11.5

11. What is the major product of the following reaction?

Klein, Organic Chemistry 1e

Answer: a.

For more examples of this type of problem, see Skillbuilder

11.5.

Klein, Organic Chemistry 1e

Alternate Answers:

Section: 11.5
11. What is the major product of the following reaction?

A. A
B. B
C. C
D. D
E. E and F
Klein, Organic Chemistry 1e
Answer: a

Klein, Organic Chemistry 1e

Section: 11.6

12. If a reactant has only one stereocenter and a radical

reaction occurs at that stereocenter, the reaction will
produce a  ___ .

 a. racemic product

 b. product with inversion of configuration

 c. product with retention of configuration

 d. Markovnikov product

Klein, Organic Chemistry 1e

Answer: a.
 

Klein, Organic Chemistry 1e

Section: 11.6

13. List ALL the major products of the following reaction?

Klein, Organic Chemistry 1e

Answer: a, b.
 
For more examples of this type of problem, see Skillbuilder
11.6.

Klein, Organic Chemistry 1e

Alternate Answers:

Section: 11.6
13. List ALL the major products of the following reaction?

A. A
B. B
C. C
D. D
E. A and B

Klein, Organic Chemistry 1e

Answer: e

Klein, Organic Chemistry 1e

Section: 11.7

14. What is the major product of the following reaction?

Klein, Organic Chemistry 1e

Answer: a.
 
For more examples of this type of problem, see Skillbuilder
11.7.

Klein, Organic Chemistry 1e

Alternate Answers:

Section: 11.7
14. What is the major product of the following reaction?

A. A
B. B
C. C
D. D
E. E and F

Klein, Organic Chemistry 1e

Answer: a

Klein, Organic Chemistry 1e

Section: 11.7

15. What is the major product of the following reaction?

NBS, h, CCl4

A. B. C. D.
Br
Br

Br Br

Klein, Organic Chemistry 1e

Answer: a.

For more examples of this type of problem, see Skillbuilder

11.7.

Klein, Organic Chemistry 1e

Section: 11.8

16. The ozone layer protects us from harmful _________

radiation  that can cause skin cancer.
 
The ozone layer has been depleted by chemicals  released
from air conditioners and refrigerator refrigerants that will
generate __________,

a. ultraviolet, bromine radicals

 b. ultraviolet, chlorine radicals

 c. infrared, bromine radicals

 d. infrared, chlorine radicals

Klein, Organic Chemistry 1e

Answer: b.
 

Klein, Organic Chemistry 1e

Section: 11.8 
 
17. UV light from the sun is absorbed and causes an
________ molecule to split into two pieces
 
Those two pieces recombine to release energey and
regenerate the_________ molecule.
 
__________ radicals from CFCs decompose ozone instead
of the sun light allowing the sunlight to reach the surface of
the earth unfiltered.

a. ozone, ozone, chlorine

 b. oxygen, ozone, chlorine

 c. oxygen, oxygen, chlorine

 d. ozone, ozone, chlorine

Klein, Organic Chemistry 1e

Answer: a

Klein, Organic Chemistry 1e

Section: 11.10

18. What are the products of the following reaction?

Klein, Organic Chemistry 1e

Answer: a, b, c, d.

This reaction produces racemic mixtures. For more examples

of this type of problem, see Skillbuilder 11.8.

Klein, Organic Chemistry 1e

Alternate Answers:

Section: 11.10
18. What are the products of the following reaction?

A. A, B
B. C, D
C. A, B, C
D. B, C, D
E. A, B, C, D
Klein, Organic Chemistry 1e
Answer: e

Klein, Organic Chemistry 1e