Question 1

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 2

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

Question 3

What is the characteristic of a radical chain termination 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 4

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 5

Consider the reaction below to answer the following question(s).  
-The name of one of the minor products of this reaction is____________________.

Accepted Answer

1-bromo-2-hexene 1-b

Question 6

Homolytic cleavage of CH3CH2CH2-O-O-CH2CH3 would produce two identical radicals.

Accepted Answer

A) True 
 B)False

Question 7

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 8

Consider the reaction below to answer the following question(s).  
-The number of allylic positions in compound A is ______.

Accepted Answer

The answer of Consider the reaction below to answer the...

Question 9

Provide the IUPAC name of the following compound.

Accepted Answer

(S)-4-brom

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

Which of the following statements is not true regarding the halogenation of alkanes upon treatment with halogen and light?

Accepted Answer

A) Bromination is more selective for 3$\circ$ positions than chlorination. 
B) The reaction proceeds via a radical intermediate. 
C) The reaction proceeds via a chain reaction. 
D) This is a useful process for the formation of fluorides, chlorides, bromides and iodides. 
A) Bromination is more selective for 3$\circ$ positions than chlorination. 
B) The reaction proceeds via a radical intermediate. 
C) The reaction proceeds via a chain reaction. 
D) This is a useful process for the formation of fluorides, chlorides, bromides and iodides.

Question 12

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 molecule. 
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 molecule.

Question 13

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 14

Which of the following accounts for the anti-Markovnikov regiochemistry of the reaction of an alkene with HBr in the presence of peroxides?

Accepted Answer

A) The alkene reacts with HBr to give a carbocation. 
B) The alkene reacts with a bromine atom to give a radical. 
C) The alkene reacts with a hydrogen atom to give a radical. 
D) The alkene reacts with peroxide to five an allylic radical. 
A) The alkene reacts with HBr to give a carbocation. 
B) The alkene reacts with a bromine atom to give a radical. 
C) The alkene reacts with a hydrogen atom to give a radical. 
D) The alkene reacts with peroxide to five an allylic radical.

Question 15

The IUPAC name for the following substance is 6-methyl-2-bromoheptane.

Accepted Answer

A) True 
 B)False

Question 16

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 planar 
A) tetrahedral 
B) trigonal planar 
C) trigonal pyramidal 
D) square planar

Question 17

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 18

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

Accepted Answer

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

Question 19

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-pentene 
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-pentene

Question 20

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

Exam 8: Haloalkanes, Halogenation, and Radical Reactions

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

What is the characteristic of a radical chain termination step?

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

Consider the reaction below to answer the following question(s). -The name of one of the minor products of this reaction is____________________.

Homolytic cleavage of CH3CH2CH2-O-O-CH2CH3 would produce two identical radicals.

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

Consider the reaction below to answer the following question(s). -The number of allylic positions in compound A is ______.

Provide the IUPAC name of the following compound.

What is the characteristic of a radical chain initiation step?

Which of the following statements is not true regarding the halogenation of alkanes upon treatment with halogen and light?

What is the characteristic of a radical chain propagation step?

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

Which of the following accounts for the anti-Markovnikov regiochemistry of the reaction of an alkene with HBr in the presence of peroxides?

The IUPAC name for the following substance is 6-methyl-2-bromoheptane.

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

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

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

What is the IUPAC name of the following compound?

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

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

Filters

Homolytic cleavage of CH₃CH₂CH₂-O-O-CH₂CH₃ would produce two identical radicals.