Question 1

What is the reactive intermediate in the autooxidation of cyclohexene?

Accepted Answer

A)  an allylic radical 
B)  a 2$\degree$ carbocation 
C)  a carbocation 
D)  a diene 
A)  an allylic radical 
B)  a 2$\degree$ carbocation 
C)  a carbocation 
D)  a diene A

Question 2

How many p-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 
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 A

Question 3

What is the correct assignment of the names of the following compounds?

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 = trichlor 
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 = trichlor C

Question 4

Which of the following statements is not true about the allyl radical

Accepted Answer

A)  the carbon-carbon bond lengths are identical 
B)  the unpaired electron density is shared between carbons 1 and 2. 
C)  it undergoes reaction with bromine to give a single product 
D)  it is formed by abstraction of a hydrogen atom from the methyl group of propene 
A)  the carbon-carbon bond lengths are identical 
B)  the unpaired electron density is shared between carbons 1 and 2. 
C)  it undergoes reaction with bromine to give a single product 
D)  it is formed by abstraction of a hydrogen atom from the methyl group of propene

Question 5

Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

Accepted Answer

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

Question 6

How many electrons does the allyl radical have in p orbitals

Accepted Answer

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

Question 7

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 anti-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 anti-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 8

What is the IUPAC name of the following compound?

Accepted Answer

A)  (R)-1-chloro-3-methyl-2-cyclohexene 
B)  (S)-1-chloro-3-methyl-2-cyclohexene 
C)  (R)-3-chloro-1-methylcyclohexene 
D)  (S)-3-chloro-1-methylcyclohexene 
A)  (R)-1-chloro-3-methyl-2-cyclohexene 
B)  (S)-1-chloro-3-methyl-2-cyclohexene 
C)  (R)-3-chloro-1-methylcyclohexene 
D)  (S)-3-chloro-1-methylcyclohexene

Question 9

Which halogen is most useful in the regioselective radical halogenation of alkenes??

Accepted Answer

A)  fluorine 
B)  chlorine 
C)  bromine 
D)  iodine 
A)  fluorine 
B)  chlorine 
C)  bromine 
D)  iodine

Question 10

What is the characteristic of a radical chain initiation step?

Accepted Answer

A)  radicals are formed 
B)  substitution products 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 molecule 
A)  radicals are formed 
B)  substitution products 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 molecule

Question 11

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

Accepted Answer

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

Question 12

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 13

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 14

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 15

Provide the IUPAC name of the following compound (shown as a Fischer projection).

Accepted Answer

The answer of Provide the IUPAC name of the following...

Question 16

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

Accepted Answer

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

Question 17

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

Accepted Answer

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

Question 18

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-hexene 
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-hexene

Question 19

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

Accepted Answer

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

Question 20

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

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 4 
A)  only 1 and 2 
B)  only 1 and 4 
C)  only 2 and 3 
D)  a mixture of 1, 2, 3, and 4

Exam 8: Haloalkanes, Halogenation, and Radical Reactions

What is the reactive intermediate in the autooxidation of cyclohexene?

How many p-bonding, non-bonding, and antibonding orbitals does the allyl radical possess?

What is the correct assignment of the names of the following compounds?

Which of the following statements is not true about the allyl radical

Which of the following alkenes undergoes allylic bromination to form a single monobrominated product?

How many electrons does the allyl radical have in p orbitals

Which of the following statements is not true?

What is the IUPAC name of the following compound?

Which halogen is most useful in the regioselective radical halogenation of alkenes??

What is the characteristic of a radical chain initiation step?

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

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

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

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

Provide the IUPAC name of the following compound (shown as a Fischer projection).

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

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

What is the IUPAC name of the following compound?

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

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

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

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