Question 1

In which of the following alkene addition reactions will carbocation rearrangements occur?

Accepted Answer

A)  Addition of Br2 and H2O 
B)  Addition of Br2 
C)  Addition of Cl2 and H2O 
D)  Addition of H2O in the presence of H2SO4 
A)  Addition of Br2 and H2O 
B)  Addition of Br2 
C)  Addition of Cl2 and H2O 
D)  Addition of H2O in the presence of H2SO4

Question 2

Which of the following alkenes are internal alkenes?

Accepted Answer

A)  I and II 
B)  II and III 
C)  I and III 
D)  II and IV 
A)  I and II 
B)  II and III 
C)  I and III 
D)  II and IV

Question 3

Which of the following reaction conditions would result in anti-Markovnikov addition to an alkene?

Accepted Answer

A)  H2O/H3O+ 
B)  HBr 
C)  HCl 
D)  [1] BH3; [2] H2O2/HO- 
A)  H2O/H3O+ 
B)  HBr 
C)  HCl 
D)  [1] BH3; [2] H2O2/HO-

Question 4

What is (are) the missing reagent(s) in the following reaction?

Accepted Answer

A)  Br2/CCl4 
B)  NBS, DMSO/H2O 
C)  [1] Br2; [2] H2O 
D)  [1] BH3; [2] H2O2/HO- 
A)  Br2/CCl4 
B)  NBS, DMSO/H2O 
C)  [1] Br2; [2] H2O 
D)  [1] BH3; [2] H2O2/HO-

Question 5

What is the best choice of reagent to accomplish the following transformation?

Accepted Answer

A)  HBr 
B)  Br2, H2O 
C)  Br2 
D)  H2O2/Br2 
A)  HBr 
B)  Br2, H2O 
C)  Br2 
D)  H2O2/Br2

Question 6

What is the IUPAC name for the following compound?

Accepted Answer

A)  4-Ethyl-3-methyl-1-octen-5-ol 
B)  3-Ethyl-4-methyl-2-octen-5-ol 
C)  5-Ethyl-6-methyl-7-octen-4-ol 
D)  4-Ethyl-6-methyl-1-octen-5-ol 
A)  4-Ethyl-3-methyl-1-octen-5-ol 
B)  3-Ethyl-4-methyl-2-octen-5-ol 
C)  5-Ethyl-6-methyl-7-octen-4-ol 
D)  4-Ethyl-6-methyl-1-octen-5-ol

Question 7

Markovnikov addition of HBr to CH3CH=CH2 involves which of the following?

Accepted Answer

A)  Initial attack by bromide anion (Br-). 
B)  Initial attack by bromine radical (Br•). 
C)  Formation of a primary carbocation. 
D)  Formation of a secondary carbocation. 
A)  Initial attack by bromide anion (Br-). 
B)  Initial attack by bromine radical (Br•). 
C)  Formation of a primary carbocation. 
D)  Formation of a secondary carbocation.

Question 8

Predict the product(s) of the following reaction.

Accepted Answer

A)  Only I and II 
B)  Only I and III 
C)  Only II and III 
D)  Only III and IV 
A)  Only I and II 
B)  Only I and III 
C)  Only II and III 
D)  Only III and IV

Question 9

What is the starting material in the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 10

What is (are) the major product(s) obtained from the following reaction?

Accepted Answer

A)  Only I 
B)  Only II 
C)  Only III 
D)  Only I and II 
A)  Only I 
B)  Only II 
C)  Only III 
D)  Only I and II

Question 11

Calculate the degree of unsaturation for a molecule with molecular formula C8H9N.

Accepted Answer

A)  2 
B)  3 
C)  4 
D)  5 
A)  2 
B)  3 
C)  4 
D)  5

Question 12

What is the major product of the following reaction?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 13

Which of the following alkenes reacts fastest with HCl?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 14

Predict the product of the following reaction, ignoring stereochemistry.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 15

Rank the carbocation in order of increasing stability, putting the least stable first.

Accepted Answer

A)  III < I < II 
B)  III < II < I 
C)  I < II < III 
D)  I < III < II 
A)  III < I < II 
B)  III < II < I 
C)  I < II < III 
D)  I < III < II

Question 16

What type of reactive intermediate is formed in the reaction of an alkene with Br2 and H2O to give a bromohydrin?

Accepted Answer

A)  Carbanion 
B)  Radical 
C)  Carbocation 
D)  Cyclic bromonium ion 
A)  Carbanion 
B)  Radical 
C)  Carbocation 
D)  Cyclic bromonium ion

Question 17

What is the common name of the following compound?

Accepted Answer

A)  2-Vinylcyclohexene 
B)  2-Allylcyclohexene 
C)  1-Allylcyclohexene 
D)  1-Vinylcyclohexene 
A)  2-Vinylcyclohexene 
B)  2-Allylcyclohexene 
C)  1-Allylcyclohexene 
D)  1-Vinylcyclohexene

Question 18

Which of the following alkenes are terminal alkenes?

Accepted Answer

A)  I and II 
B)  II and III 
C)  I and IV 
D)  I and III 
A)  I and II 
B)  II and III 
C)  I and IV 
D)  I and III

Question 19

What is the IUPAC name for the following compound?

Accepted Answer

A)  5-Methyl-5-hexen-2-ol 
B)  6-Methyl-6-hepten-2-ol 
C)  6-Hydroxy-2-methylheptene 
D)  6-Hydroxy-2-methyl-1-heptene 
A)  5-Methyl-5-hexen-2-ol 
B)  6-Methyl-6-hepten-2-ol 
C)  6-Hydroxy-2-methylheptene 
D)  6-Hydroxy-2-methyl-1-heptene

Question 20

Which of the following statements about alkenes is not true?

Accepted Answer

A)  They are less reactive than alkanes. 
B)  They can exist as cis/trans isomers. 
C)  The bond angle around the C-C double bond is approximately 120°. 
D)  The carbon of the C-C double bond is sp2 hybridized. 
A)  They are less reactive than alkanes. 
B)  They can exist as cis/trans isomers. 
C)  The bond angle around the C-C double bond is approximately 120°. 
D)  The carbon of the C-C double bond is sp2 hybridized.

Exam 10: Alkenes

In which of the following alkene addition reactions will carbocation rearrangements occur?

Which of the following alkenes are internal alkenes?

Which of the following reaction conditions would result in anti-Markovnikov addition to an alkene?

What is (are) the missing reagent(s) in the following reaction?

What is the best choice of reagent to accomplish the following transformation?

What is the IUPAC name for the following compound?

Markovnikov addition of HBr to CH3CH=CH2 involves which of the following?

Predict the product(s) of the following reaction.

What is the starting material in the following reaction?

What is (are) the major product(s) obtained from the following reaction?

Calculate the degree of unsaturation for a molecule with molecular formula C8H9N.

What is the major product of the following reaction?

Which of the following alkenes reacts fastest with HCl?

Predict the product of the following reaction, ignoring stereochemistry.

Rank the carbocation in order of increasing stability, putting the least stable first.

What type of reactive intermediate is formed in the reaction of an alkene with Br2 and H2O to give a bromohydrin?

What is the common name of the following compound?

Which of the following alkenes are terminal alkenes?

What is the IUPAC name for the following compound?

Which of the following statements about alkenes is not true?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

Markovnikov addition of HBr to CH₃CH=CH₂ involves which of the following?

Calculate the degree of unsaturation for a molecule with molecular formula C₈H₉N.

What type of reactive intermediate is formed in the reaction of an alkene with Br₂ and H₂O to give a bromohydrin?