Question 1

What is the IUPAC name of the following compound?

Accepted Answer

A)  (R) -2-bromo-2-vinylpentane
B)  (S) -2-bromo-2-vinylpentane
C)  (S) -3-bromo-3-propyl-1-butene
D)  (R) -3-bromo-3-methyl-1-hexeneE) None of the above
F) B) and C)

Question 2

What is the major product formed upon radical bromination of (S) -3-methylhexane?

Accepted Answer

A)  (S)  3-bromo-3-methylhexane
B)  (R)  3-bromo-3-methylhexane
C)  a mixture of (R)  and (S)  3-bromo-3-methylhexane
D)  (3R)  1-bromo-3-methylhexaneE) All of the above
F) B) and D)

Question 3

How many electrons does the allyl radical have in p orbitals

Accepted Answer

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

Question 4

What is the correct assignment of the names of the following compounds?
1) CH3Cl
2) CH2Cl2
3) CHCl3

Accepted Answer

A)  1 = methyl chloride; 2 = chloroform; 3 = methylene chloride
B)  1 = trichlor; 2 = chloroform; 3 = methylene chloride
C)  1 = methyl chloride; 2 = methylene chloride; 3 = chloroform
D)  1 = chloroform; 2 = methylene chloride; 3 = trichlorE) B) and C)
F) A) and D)

Question 5

How many  π\piπ -bonding, non-bonding, and antibonding orbitals does the allyl radical possess?

Accepted Answer

A)  one bonding, one nonbonding, and one antibonding
B)  two bonding, no nonbonding, and no antibonding
C)  two bonding, one nonbonding, and no antibonding
D)  three bonding, no nonbonding, and no antibonding E) C) and D)
F) None of the above

Question 6

The IUPAC name for the following substance is trans-1-bromo-4-methylcyclohexane.

Accepted Answer

A) True 
 B)False

Question 7

Consider the following reaction.  In the presence of peroxides, the major product of the reaction is shown below.

Accepted Answer

A) True 
 B)False  True

Question 8

What are the major products formed upon treatment of (E) -3-methyl-2-hexene with HBr in the presence of peroxides?
1) (S,S) -2-bromo-3-methylhexane
2) (S,R) -2-bromo-2-methylhexane
3) (R,S) -2-bromo-2-methylhexane
4) (R,R) -2-bromo-2-methylhexane

Accepted Answer

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

Question 9

Which of the following is an accurate statement of Hammond's postulate?

Accepted Answer

A)  The transition state of an exothermic reaction will resemble the starting materials (reactants)  more than the product.
B)  The transition state of an exothermic reaction will resemble the products more than the starting materials (reactants) .
C)  The transition state of an endothermic reaction will resemble the starting materials (reactants)  more than the product.
D)  the difference in energy between the starting materials (reactants)  and transition state controls the rate of a reaction.E) A) and B)
F) A) and C) A

Question 10

The number of possible monobromination products, including cis-trans isomers, of methylcyclopentane is ______.

Accepted Answer

The answer of The number of possible monobromination products, including...

Question 11

Autoxidation occurs by a radical chain mechanism that requires oxygen and an initiator.

Accepted Answer

A) True 
 B)False

Question 12

In the chlorination of methane, the propagation steps involve forming methyl, chlorine, and hydrogen radicals.

Accepted Answer

A) True 
 B)False

Question 13

The major products of the reaction would be formed from the radical intermediate numbered _____ as shown below.
1.  2.

Accepted Answer

The answer of The major products of the reaction would...

Question 14

What is the major product of autooxidation of cyclohexene?

Accepted Answer

A)  1
B)  2
C)  3
D)  4E) C) and D)
F) A) and B)

Question 15

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 16

Which of the following statements is not true?

Accepted Answer

A)  Bromine radicals add to the least substituted end of a carbon-carbon double bond of an alkene.
B)  The major non-Markovnikov product obtained upon addition of HBr to alkenes in the presence of a peroxide is formed in a radical termination step.
C)  Two radicals combine in radical termination steps.
D)  Alkoxy radicals remove a hydrogen atom from HBr to give an alcohol and a bromine atom.E) C) and D)
F) A) and B)

Question 17

During bromination using NBS, the addition product is not observed because the rate of addition is _______than the rate of the chain propagation steps.

Accepted Answer

The answer of During bromination using NBS, the addition product...

Question 18

What type of reactive intermediate is formed in the reaction of propene with hydrogen bromide in the presence of peroxides to give 1-bromopropane?

Accepted Answer

A)  1.0 ∘\circ∘  radical
B)  1 ∘\circ∘  carbocation
C)  1 ∘\circ∘  radical
D)  2 ∘\circ∘  radical E) A) and B)
F) A) and C)

Question 19

The number of possible dibromination products of 2-methylpropane is______.

Accepted Answer

The answer of The number of possible dibromination products of...

Question 20

Which of the following statements is not true?

Accepted Answer

A)  Homolytic cleavage of a bond in a neutral molecule gives two radicals.
B)  Radicals have one or more unpaired electrons.
C)  Movement of single electrons is depicted using a "fishhook arrow".
D)  The C-F bond is the weakest bond between carbon atom and a halogen.E) A) and B)
F) All of the above D

Exam 8: Haloalkanes, Halogenation, and Radical Reactions

What is the IUPAC name of the following compound?

Correct AnswerverifiedShow Answer

What is the major product formed upon radical bromination of (S) -3-methylhexane?

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How many electrons does the allyl radical have in p orbitals

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What is the correct assignment of the names of the following compounds? 1) CH3Cl 2) CH2Cl2 3) CHCl3

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How many π\piπ -bonding, non-bonding, and antibonding orbitals does the allyl radical possess?

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The IUPAC name for the following substance is trans-1-bromo-4-methylcyclohexane.

Correct AnswerverifiedShow Answer

Consider the following reaction. In the presence of peroxides, the major product of the reaction is shown below.

Correct AnswerverifiedTrue

What are the major products formed upon treatment of (E) -3-methyl-2-hexene with HBr in the presence of peroxides? 1) (S,S) -2-bromo-3-methylhexane 2) (S,R) -2-bromo-2-methylhexane 3) (R,S) -2-bromo-2-methylhexane 4) (R,R) -2-bromo-2-methylhexane

Correct AnswerverifiedShow Answer

Which of the following is an accurate statement of Hammond's postulate?

Correct AnswerverifiedA

The number of possible monobromination products, including cis-trans isomers, of methylcyclopentane is ______.

Correct AnswerverifiedShow Answer

Autoxidation occurs by a radical chain mechanism that requires oxygen and an initiator.

Correct AnswerverifiedShow Answer

In the chlorination of methane, the propagation steps involve forming methyl, chlorine, and hydrogen radicals.

Correct AnswerverifiedShow Answer

The major products of the reaction would be formed from the radical intermediate numbered _____ as shown below. 1. 2.

Correct AnswerverifiedShow Answer

What is the major product of autooxidation of cyclohexene?

Correct AnswerverifiedShow Answer

What is the major organic product obtained from the following reaction?

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Which of the following statements is not true?

Correct AnswerverifiedShow Answer

During bromination using NBS, the addition product is not observed because the rate of addition is _______than the rate of the chain propagation steps.

Correct AnswerverifiedShow Answer

What type of reactive intermediate is formed in the reaction of propene with hydrogen bromide in the presence of peroxides to give 1-bromopropane?

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The number of possible dibromination products of 2-methylpropane is______.

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Which of the following statements is not true?

Correct AnswerverifiedD

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What is the correct assignment of the names of the following compounds? 1) CH₃Cl 2) CH₂Cl₂ 3) CHCl₃

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How many $\pi$ -bonding, non-bonding, and antibonding orbitals does the allyl radical possess?

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True

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A

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D