Question 1

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) All of the above

Question 2

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) A) and C)
F) A) and B)

Question 3

How many products,including stereoisomers,are formed when 2-methylpent-2-ene is treated with HBr in presence of peroxides?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) All of the above
F) None of the above

Question 4

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 B)
F) B) and C)

Question 5

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) B) and D)

Question 6

How many products,including stereoisomers,are formed when (R) -2,4-dimethylhex-2-ene is treated with HBr in presence of peroxides?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) B) and D)
F) All of the above

Question 7

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 C)
F) B) and D)

Question 8

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

Accepted Answer

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

Question 9

What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide (NBS) to give 3-bromo-1-propene?

Accepted Answer

A)  Cyclic bromonium ion
B)  Allylic carbocation
C)  Allylic carbanion
D)  Allylic radicalE) B) and D)
F) None of the above

Question 10

Which of the following statements is (are) true about free radical halogenation of alkanes?

Accepted Answer

A)  The first of the chain-propagating steps is rate-determining.
B)  The reaction proceeds by way of a flat sp2 hybridized free radical.
C)  The chain-initiating step involves cleavage of a carbon-hydrogen bond to afford a carbon radical and a hydrogen atom.
D)  Statements (The first of the chain-propagating steps is rate-determining) and (The reaction proceeds by way of a flat sp2 hybridized free radical) are both true.E) All of the above
F) None of the above

Question 11

Find the major product of the following reaction.

Accepted Answer

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

Question 12

What is the product in the following sequence of reactions?

Accepted Answer

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

Question 13

Determine the product(s) of the following reaction.

Accepted Answer

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

Question 14

Which of the following statements about chlorination and bromination is true?

Accepted Answer

A)  Bromination is unselective,yielding a mixture of products.
B)  Chlorination is often selective,yielding one major product.
C)  Chlorination is faster than bromination.
D)  Bromination is faster than chlorination.E) B) and C)
F) A) and C)

Question 15

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) B) and C)
F) None of the above

Question 16

Determine the monochlorination product(s) .

Accepted Answer

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

Question 17

How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH3) 2CHCH2CH3 with Cl2 and hn?

Accepted Answer

A)  2
B)  3
C)  4
D)  5E) A) and B)
F) None of the above

Question 18

Determine the product of the following reaction.

Accepted Answer

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

Question 19

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 20

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) C) and D)
F) B) and D) A

Exam 13: Radical Reactions

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

Correct AnswerverifiedShow Answer

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

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How many products,including stereoisomers,are formed when 2-methylpent-2-ene is treated with HBr in presence of peroxides?

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

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 products,including stereoisomers,are formed when (R) -2,4-dimethylhex-2-ene is treated with HBr in presence of peroxides?

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

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

Correct AnswerverifiedD

What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide (NBS) to give 3-bromo-1-propene?

Correct AnswerverifiedShow Answer

Which of the following statements is (are) true about free radical halogenation of alkanes?

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Find the major product of the following reaction.

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What is the product in the following sequence of reactions?

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Determine the product(s) of the following reaction.

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Which of the following statements about chlorination and bromination is true?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

Determine the monochlorination product(s) .

Correct AnswerverifiedD

How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH3) 2CHCH2CH3 with Cl2 and hn?

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Determine the product of the following reaction.

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What is the product in the following sequence of reactions?

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) :

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

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D

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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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D

How many monochlorination products can be formed (constitutional isomers only) from the reaction of (CH₃) ₂CHCH₂CH₃ with Cl₂ and hn?

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A