Question 1

How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH3CH2CH2CH2CH2CH3 with Cl2 and hn?

Accepted Answer

A)  3
B)  4
C)  5
D)  6E) A) and B)
F) A) and C)

Question 2

What is the product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) C) and D)
F) B) and C)

Question 3

Which of the following would be the fastest to form a radical?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and D)
F) A) and B)

Question 4

Determine the monochlorination product(s) .

Accepted Answer

A)  Only I
B)  Only II
C)  Only III
D)  Only I and IIE) B) and C)
F) B) and D)

Question 5

How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of pentane with Cl2 and hn?

Accepted Answer

A)  2
B)  3
C)  4
D)  5E) A) and D)
F) A) and C)

Question 6

Which of the following statements about radicals is true?

Accepted Answer

A)  Cleavage of a stronger bond forms the more stable radical.
B)  The stability of a radical increases as the number of alkyl groups bonded to the radical carbon decreases.
C)  The higher the bond dissociation energy for a C-H bond,the more stable the resulting carbon radical.
D)  Less stable radicals generally do not rearrange to more stable radicals.E) All of the above
F) B) and C)

Question 7

A possible reaction of ethane with chlorine is shown below.  This reaction could conceivably occur by the following chain mechanisms [1],[2],and [3].Determine DH for step [2].  Bond dissociation energies (kcal/mol) :

Accepted Answer

A)  -5 kcal/mol
B)  +58 kcal/mol
C)  -28 kcal/mol
D)  None of the choices are correct.E) A) and B)
F) None of the above

Question 8

Which steps are the rate-determining step in the mechanism of radical halogenation?

Accepted Answer

A)  Initiation
B)  Propagation
C)  Termination
D)  Initiation and propagationE) A) and C)
F) A) and B) B

Question 9

Which of the labeled hydrogens is most easily abstracted in a free radical bromination reaction? a B) Hb C) Hc D) Hd" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  Ha
B)  Hb
C)  Hc
D)  HdE) A) and B)
F) A) and C) B

Question 10

Rank the following radicals in order of increasing stability,putting the least stable first.

Accepted Answer

A)  III
B)  I 
C)  III 
D)  I < III < IIE) A) and B)
F) A) and C)

Question 11

Which of the following compounds contain secondary (2°) radical carbons?

Accepted Answer

A)  Only I
B)  Only II
C)  Only III
D)  Only II and IVE) B) and C)
F) A) and D)

Question 12

Which of the following compounds contain tertiary (3°) radical carbons?

Accepted Answer

A)  Only I
B)  Only II
C)  Only III
D)  Only II and IVE) All of the above
F) C) and D)

Question 13

How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl2 and hn?

Accepted Answer

A)  2
B)  3
C)  4
D)  5E) A) and B)
F) A) and C)

Question 14

What is the product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and C)
F) A) and D)

Question 15

Which of the following statements about the stereochemistry of halogenation reactions is true?

Accepted Answer

A)  An achiral starting material always gives an achiral product only.
B)  An achiral starting material always gives a racemic product only.
C)  The configuration at a stereogenic center of a product must change even if a reaction does not occur at a stereogenic center.
D)  An achiral starting material always gives either an achiral or a racemic product.E) A) and D)
F) C) and D)

Question 16

A possible reaction of ethane with chlorine is shown below.  This reaction could conceivably occur by the following chain mechanisms [1],[2],and [3].The chain propagating step(s) is (are) ________.

Accepted Answer

A)  Only [1] and [2]
B)  Only [2] and [3]
C)  Only [1] and [3]
D)  Only [3]E) All of the above
F) A) and B)

Question 17

What is the product in the following sequence of reactions?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and C)
F) None of the above

Question 18

Which of the following compounds contain primary (1°) radical carbons?

Accepted Answer

A)  Only I
B)  Only II
C)  Only III
D)  Only II and IVE) A) and D)
F) A) and B)

Question 19

Select the route that would most likely produce the desired results from the given starting material. 2SO4 and heat; (2) HBr II.(1) KOH in ethanol; (2) HBr III) (1) H2SO4 and heat; (2) HBr + peroxides IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides A) I B) II C) III D) IV" class="answers-bank-image d-inline" rel="preload" > I.(1) H2SO4 and heat; (2) HBr II.(1) KOH in ethanol; (2) HBr
III) (1) H2SO4 and heat; (2) HBr + peroxides
IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) C) and D) D

Question 20

How many monochlorination products,including stereoisomers,are formed from (S,S) -1,2-dimethylcyclopropane?

Accepted Answer

A)  4
B)  3
C)  6
D)  5E) A) and B)
F) A) and C)

Exam 13: Radical Reactions

How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH3CH2CH2CH2CH2CH3 with Cl2 and hn?

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

Which of the following would be the fastest to form a radical?

Correct AnswerverifiedShow Answer

Determine the monochlorination product(s) .

Correct AnswerverifiedShow Answer

How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of pentane with Cl2 and hn?

Correct AnswerverifiedShow Answer

Which of the following statements about radicals is true?

Correct AnswerverifiedShow Answer

A possible reaction of ethane with chlorine is shown below. This reaction could conceivably occur by the following chain mechanisms [1],[2],and [3].Determine DH for step [2]. Bond dissociation energies (kcal/mol) :

Correct AnswerverifiedShow Answer

Which steps are the rate-determining step in the mechanism of radical halogenation?

Correct AnswerverifiedB

Which of the labeled hydrogens is most easily abstracted in a free radical bromination reaction?

Correct AnswerverifiedB

Rank the following radicals in order of increasing stability,putting the least stable first.

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Which of the following compounds contain secondary (2°) radical carbons?

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Which of the following compounds contain tertiary (3°) radical carbons?

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How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl2 and hn?

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

Which of the following statements about the stereochemistry of halogenation reactions is true?

Correct AnswerverifiedShow Answer

A possible reaction of ethane with chlorine is shown below. This reaction could conceivably occur by the following chain mechanisms [1],[2],and [3].The chain propagating step(s) is (are) ________.

Correct AnswerverifiedShow Answer

What is the product in the following sequence of reactions?

Correct AnswerverifiedShow Answer

Which of the following compounds contain primary (1°) radical carbons?

Correct AnswerverifiedShow Answer

Select the route that would most likely produce the desired results from the given starting material. I.(1) H2SO4 and heat; (2) HBr II.(1) KOH in ethanol; (2) HBr III) (1) H2SO4 and heat; (2) HBr + peroxides IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides

Correct AnswerverifiedD

How many monochlorination products,including stereoisomers,are formed from (S,S) -1,2-dimethylcyclopropane?

Correct AnswerverifiedShow Answer

How many monochlorination products can be formed (constitutional isomers only) from the reaction of CH₃CH₂CH₂CH₂CH₂CH₃ with Cl₂ and hn?

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How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of pentane with Cl₂ and hn?

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B

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B

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How many monochlorination products (constitutional isomers and stereoisomers) are formed from the reaction of butane with Cl₂ and hn?

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Select the route that would most likely produce the desired results from the given starting material. I.(1) H₂SO₄ and heat; (2) HBr II.(1) KOH in ethanol; (2) HBr III) (1) H₂SO₄ and heat; (2) HBr + peroxides IV) (1) potassium tert-butoxide in tert-butanol; (2) HBr + peroxides

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D

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