Question 1

Provide the IUPAC name of the following compound.

Accepted Answer

(S)-2-chlo

Question 2

The boiling points of alkanes increase as the length of the carbon chain increases but decrease as the amount of branching increases.

Accepted Answer

A) True 
 B)False

Question 3

The structure of (S)-2-bromobutane is given below.

Accepted Answer

A) True 
 B)False

Question 4

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 5

Which of the following has the list of compounds in the correct order of decreasing polarity (more polar > less polar)?

Accepted Answer

A) CCl4 > CHCl3 > CH2Cl2 
B) CH2Cl2 > CHCl3 > CCl4 
C) CCl4 > CH2Cl2 > CHCl3 
D) CHCl3 > CCl4 > CH2Cl2 
A) CCl4 > CHCl3 > CH2Cl2 
B) CH2Cl2 > CHCl3 > CCl4 
C) CCl4 > CH2Cl2 > CHCl3 
D) CHCl3 > CCl4 > CH2Cl2

Question 6

What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide to give 3-bromo-1-propene?

Accepted Answer

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

Question 7

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

Accepted Answer

A) 3$\circ$ C 2p atomic orbital + 3$\circ$ C sp2 atomic orbital 
B) 3$\circ$ C 2p atomic orbital + methyl C-H $\sigma$ molecular orbital 
C) 3$\circ$C sp2 atomic orbital + methyl C-H $\sigma$ molecular orbital 
D) 3$\circ$ C 2p atomic orbital + methyl C 2s atomic orbital 
A) 3$\circ$ C 2p atomic orbital + 3$\circ$ C sp2 atomic orbital 
B) 3$\circ$ C 2p atomic orbital + methyl C-H $\sigma$ molecular orbital 
C) 3$\circ$C sp2 atomic orbital + methyl C-H $\sigma$ molecular orbital 
D) 3$\circ$ C 2p atomic orbital + methyl C 2s atomic orbital

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

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 10

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

Accepted Answer

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

Question 11

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 12

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 13

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

Accepted Answer

A) "s" 
B) "p" 
C) "sp3" 
D) "$\sigma$" 
A) "s" 
B) "p" 
C) "sp3" 
D) "$\sigma$"

Question 14

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 15

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

Accepted Answer

A) CH2Cl2 > CH2Br2 > CH2I2 
B) CH2Cl2 > CH2I2 > CH2Br2 
C) CH2I2 > CH2Br2 > CH2Cl2 
D) CH2I2 > CH2Cl2 > CH2Br2 
A) CH2Cl2 > CH2Br2 > CH2I2 
B) CH2Cl2 > CH2I2 > CH2Br2 
C) CH2I2 > CH2Br2 > CH2Cl2 
D) CH2I2 > CH2Cl2 > CH2Br2

Question 16

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

Exam 8: Haloalkanes, Halogenation, and Radical Reactions

Provide the IUPAC name of the following compound.

The boiling points of alkanes increase as the length of the carbon chain increases but decrease as the amount of branching increases.

The structure of (S)-2-bromobutane is given below.

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

Which of the following has the list of compounds in the correct order of decreasing polarity (more polar > less polar)?

What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide to give 3-bromo-1-propene?

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

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

Which of the following compounds is most susceptible to autooxidation?

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

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

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

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

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 density (higher density > lower density)?

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

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