Question 1

What type of orbitals overlap to provide stability to the tert-butyl radical by hyperconjugation?

Accepted Answer

A)   3 °\degree°  C 2p atomic orbital + 3 °\degree°  C sp2 atomic orbital
B)   3 °\degree°  C 2p atomic orbital + methyl C-H s molecular orbital
C)   3 °\degree°  C sp2 atomic orbital + methyl C-H s molecular orbital
D)   3 °\degree°  C 2p atomic orbital + methyl C 2s atomic orbital E) All of the above
F) A) and B)

Question 2

What is the geometry of the central carbon atom of a tert-butyl radical?

Accepted Answer

A)   tetrahedral
B)   trigonal planar
C)   trigonal pyramidal
D)   square planarE) A) and B)
F) C) and D)

Question 3

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

Accepted Answer

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

Question 4

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

Question 5

What is the IUPAC name of the following compound?

Accepted Answer

A)   (
E)  -1-chloro-1,2,3-trimethyl-1-butene
B)   (Z) -1-chloro-1,2,3-trimethyl-1-butene
C)   (
E)  -2-chloro-3,4-dimethyl-2-pentene
D)   (Z) -2-chloro-3,4-dimethyl-2-penteneE) All of the above
F) None of the above

Question 6

Which of the following alkanes does not undergo monobromination to form a single bromoalkane as the major product?

Accepted Answer

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

Question 7

What type of reactive intermediate is formed upon irradiation of a solution of toluene (Ph-CH3)  and bromine?

Accepted Answer

A)   benzylic carbocation
B)   benzylic carbanion
C)   benzylic radical
D)   cyclic bromonium ionE) A) and D)
F) All of the above

Question 8

Provide the IUPAC name of the following compound.

Accepted Answer

(S)-4-brom...

Question 9

Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point) ?

Accepted Answer

A)   2-fluoropropane > 2-chloropropane > 2-bromopropane > 2-iodopropane
B)   2-chloropropane > 2-iodopropane > 2-fluoropropane > 2-bromopropane
C)   2-iodopropane > 2-chloropropane > 2-fluoropropane > 2-bromopropane
D)   2-iodopropane > 2-bromopropane > 2-chloropropane > 2-fluoropropaneE) B) and D)
F) All of the above

Question 10

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

Question 11

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

Accepted Answer

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

Question 12

What is the correct order of stability of the following radicals (more stable > less stable) ?  less stable) ?   A)  1 > 2 > 3 B)  1 > 3 > 2 C)  3 > 1 > 2 D)  3 > 2 > 1" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 13

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

Accepted Answer

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

Question 14

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 °\degree°  radical
B)   1 °\degree°  carbocation
C)   1 °\degree°  radical.
D)   2 °\degree°  radical E) A) and B)
F) C) and D)

Question 15

Which of the following compounds is most susceptible to autooxidation?

Accepted Answer

A)   propene
B)   1,3-butadiene
C)   1,4-pentadiene
D)   1,5-hexadieneE) A) and B)
F) A) and C)

Question 16

Which of the following bonds has the lowest bond dissociation enthalpy?

Accepted Answer

A)   C-H
B)   C-F
C)   C-Br
D)   C-IE) B) and D)
F) None of the above

Question 17

What is the characteristic of a radical chain propagation step?

Accepted Answer

A)   radicals are formed
B)   byproducts are formed
C)   a radical reacts with a molecule to give a new radical and a new molecule
D)   two radicals combine to give a moleculeE) B) and C)
F) C) and D)

Question 18

What is the major product obtained from the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxides?

Accepted Answer

A)   2,3-dibromo-2-methylbutane
B)   2-bromo-3-methylbutane
C)   2-bromo-2-methylbutane
D)   (
E)  -1-bromo-2-methyl-2-buteneE) A) and B)
F) C) and D)

Question 19

Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point) ?

Accepted Answer

A)   chloromethane > chloroethane > 2-chloropropane > 2-chloro-2-methylpropane
B)   2-chloro-2-methylpropane > 2-chloropropane > chloroethane > chloromethane
C)   chloroethane > chloromethane > 2-chloro-2-methylpropane > 2-chloropropane
D)   chloromethane > 2-chloro-2-methylpropane > 2-chloropropane > chloroethaneE) B) and C)
F) B) and D)

Question 20

What are the major products formed upon treatment of (E)  3-methyl-2-hexene with HBr in the absence of peroxides?

Accepted Answer

A)   only 1
B)   only 2
C)   a mixture of 1 and 2
D)   only 3E) C) and D)
F) B) and C)

Exam 8: Haloalkanes, Halogenation, and Radical Reactions

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

Correct AnswerverifiedShow Answer

Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point) ?

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What is the IUPAC name of the following compound?

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Provide the IUPAC name of the following compound.

Correct Answerverified(S)-4-brom...View AnswerShow Answer

What type of orbitals overlap to provide stability to the tert-butyl radical by hyperconjugation?

Correct AnswerverifiedShow Answer

What type of reactive intermediate is formed upon irradiation of a solution of toluene (Ph-CH3) and bromine?

Correct AnswerverifiedShow Answer

What is the geometry of the central carbon atom of a tert-butyl radical?

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

Correct AnswerverifiedShow Answer

What is the major product obtained from the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxides?

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Which of the following compounds is most susceptible to autooxidation?

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Which of the following bonds has the lowest bond dissociation enthalpy?

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Which of the following has the list of compounds in the correct order of decreasing boiling point (higher boiling point > lower boiling point) ?

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

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Which of the following alkanes does not undergo monobromination to form a single bromoalkane as the major product?

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What are the major products formed upon treatment of (E) 3-methyl-2-hexene with HBr in the absence of peroxides?

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

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

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What is the correct order of stability of the following radicals (more stable > less stable) ?

Correct AnswerverifiedShow Answer

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

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What is the characteristic of a radical chain propagation step?

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(S)-4-brom...
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What type of reactive intermediate is formed upon irradiation of a solution of toluene (Ph-CH₃) and bromine?

Correct Answer
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