Question 1

Which of the statements about the properties of the carbon-carbon double bond is not true?

Accepted Answer

A) There is restricted rotation around the carbon-carbon double bond. 
B) Whenever the two groups on each end of a carbon-carbon double bond are the same, two diastereomers are possible. 
C) Trans alkenes are generally more stable than cis alkenes. 
D) The stability of the carbon-carbon double bond increases as the number of substituent groups increases. 
A) There is restricted rotation around the carbon-carbon double bond. 
B) Whenever the two groups on each end of a carbon-carbon double bond are the same, two diastereomers are possible. 
C) Trans alkenes are generally more stable than cis alkenes. 
D) The stability of the carbon-carbon double bond increases as the number of substituent groups increases.

Question 2

Predict 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 3

Rank the following compounds in order of decreasing stability, putting the most stable first.

Accepted Answer

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

Question 4

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 5

Which of the following statements about alkenes is true?

Accepted Answer

A) Alkenes react with nucleophiles and bases. 
B) Alkenes contain double bonds from two sp-hybridized carbon atoms. 
C) In the reactions of alkenes, the  always broken. 
D) Alkenes react with electrophiles. 
A) Alkenes react with nucleophiles and bases. 
B) Alkenes contain double bonds from two sp-hybridized carbon atoms. 
C) In the reactions of alkenes, the  always broken. 
D) Alkenes react with electrophiles.

Question 6

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 7

Rearrangements can occur in which of the following reactions?

Accepted Answer

A) Addition of Cl2 to an alkene. 
B) Addition of HOBr to an alkene. 
C) Addition of H2O/H3O+ to an alkene. 
D) None of these. 
A) Addition of Cl2 to an alkene. 
B) Addition of HOBr to an alkene. 
C) Addition of H2O/H3O+ to an alkene. 
D) None of these.

Question 8

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 9

What type of reactive intermediate is formed in the reaction of an alkene with HI to give an iodoalkane?

Accepted Answer

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

Question 10

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 11

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 12

Which of the following alkenes is an E alkene?

Accepted Answer

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

Question 13

Which of the following statements about hydroboration/oxidation of alkenes is true?

Accepted Answer

A) In hydroboration, the boron atom bonds to the more substituted carbon. 
B) Hydroboration occurs with anti addition. 
C) Oxidation occurs with retention of configuration. 
D) 9-BBN does not undergo hydroboration in the same manner as BH3. 
A) In hydroboration, the boron atom bonds to the more substituted carbon. 
B) Hydroboration occurs with anti addition. 
C) Oxidation occurs with retention of configuration. 
D) 9-BBN does not undergo hydroboration in the same manner as BH3.

Question 14

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 15

What is the IUPAC name for the following compound?

Accepted Answer

A) 1-Methylcyclopentene 
B) 2-Methyl-1-cyclopentene 
C) 1-Methylene-1-methylcyclopentane 
D) 1-Methylcyclohexene 
A) 1-Methylcyclopentene 
B) 2-Methyl-1-cyclopentene 
C) 1-Methylene-1-methylcyclopentane 
D) 1-Methylcyclohexene

Question 16

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 17

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 18

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 19

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 20

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

Exam 10: Alkenes

Which of the statements about the properties of the carbon-carbon double bond is not true?

Predict the major product of the following reaction.

Rank the following compounds in order of decreasing stability, putting the most stable first.

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

Which of the following statements about alkenes is true?

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

Rearrangements can occur in which of the following reactions?

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 HI to give an iodoalkane?

What is the common name of the following compound?

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

Which of the following alkenes is an E alkene?

Which of the following statements about hydroboration/oxidation of alkenes is true?

What is the starting material in the following reaction?

What is the IUPAC name for the following compound?

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

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

What is the IUPAC name for the following compound?

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

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

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 Related Compounds

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

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

Synthetic Polymers

Lipids

Filters

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

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