Question 1

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 2

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 > chloroethane 
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 > chloroethane

Question 3

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 4

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-hexadiene 
A)  propene 
B)  1,3-butadiene 
C)  1,4-pentadiene 
D)  1,5-hexadiene

Question 5

Provide the IUPAC name of the following compound.

Accepted Answer

(S)-4-brom

Question 6

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 7

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 8

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 9

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

Question 10

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 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

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 13

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 
A)  1$\degree$ radical 
B)  1$\degree$ carbocation 
C)  1$\degree$ radical. 
D)  2$\degree$ radical

Question 14

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 
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

Question 15

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

Question 17

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 18

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 
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

Question 19

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 ion 
A)  benzylic carbocation 
B)  benzylic carbanion 
C)  benzylic radical 
D)  cyclic bromonium ion

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

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

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

Which of the following compounds is most susceptible to autooxidation?

Provide the IUPAC name of the following compound.

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 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 absence of peroxides?

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?

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

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

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

What is the characteristic of a radical chain propagation step?

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

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

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

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

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

Filters

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