Question 1

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

Accepted Answer

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

Question 2

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

less
slower

Question 3

Provide neatly drawn resonance structures of the key intermediate in the following reaction.

Accepted Answer

The answer of Provide neatly drawn resonance structures of the...

Question 4

What is the reactive intermediate in the autooxidation of cyclohexene?

Accepted Answer

A)  an allylic radical 
B)  a 2° carbocation 
C)  a carbocation 
D)  a diene 
A)  an allylic radical 
B)  a 2° carbocation 
C)  a carbocation 
D)  a diene

Question 5

What are the major organic products obtained from the following reaction?

Accepted Answer

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

Question 6

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

Accepted Answer

A)  C−H 
B)  C−F 
C)  C−Br 
D)  C−I 
A)  C−H 
B)  C−F 
C)  C−Br 
D)  C−I

Question 7

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-fluoropropane 
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-fluoropropane

Question 8

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

Accepted Answer

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

Question 9

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

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 10

What is the structure of the key intermediate in the following reaction?

Accepted Answer

The answer of What is the structure of the key...

Question 11

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

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 12

Consider the reaction below to answer the following question(s). $\begin{array}{ccccc}
\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}&\underset{h v}{\stackrel{\text { NBS }}{\rightarrow}} &\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCHCH}_{2} \mathrm{CH}_{3}&+&\mathrm{CH}_{3} \mathrm{CHCH}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}\
&&|&&|\&&\mathrm{Br}&&\mathrm{Br}\A&&B&&C
\end{array}$

-The name of one of the minor products of this reaction is____________________.

Accepted Answer

1-bromo-2-hexene
1-b

Question 13

What type of orbital contains the unpaired electron of the tert-butyl radical?

Accepted Answer

A)  s 
B)  p 
C)  sp3 
D)  σ 
A)  s 
B)  p 
C)  sp3 
D)  σ

Question 14

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. 
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.

Question 15

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

Question 16

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-methylhexane 
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-methylhexane

Question 17

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)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 18

The products of the addition of HBr to an alkene in the presence of peroxides is accounted for by a polar reaction mechanism.

Accepted Answer

A) True 
 B)False

Question 19

What is the structure of all of the monobrominated products, including regioismers and stereoisomers, obtained from the following reaction?

Accepted Answer

The answer of What is the structure of all of...

Question 20

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

Accepted Answer

A)  1 > 2 > 3 
B)  1 > 3 > 2 
C)  3 > 1 > 2 
D)  3 > 2 > 1 
A)  1 > 2 > 3 
B)  1 > 3 > 2 
C)  3 > 1 > 2 
D)  3 > 2 > 1

Exam 8: Haloalkanes, Halogenation, and Radical Reactions

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

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

Provide neatly drawn resonance structures of the key intermediate in the following reaction.

What is the reactive intermediate in the autooxidation of cyclohexene?

What are the major organic products obtained from the following reaction?

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

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

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

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

What is the structure of the key intermediate in the following reaction?

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

Consider the reaction below to answer the following question(s). = = + = | | A B C -The name of one of the minor products of this reaction is____________________.

What type of orbital contains the unpaired electron of the tert-butyl radical?

Which of the following statements is not true?

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

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

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

The products of the addition of HBr to an alkene in the presence of peroxides is accounted for by a polar reaction mechanism.

What is the structure of all of the monobrominated products, including regioismers and stereoisomers, obtained from the following reaction?

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

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

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