Question 1

What is the major product obtained from the following reaction?

Accepted Answer

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

Question 2

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

Accepted Answer

A)  H2O, Br2 
B)  [1] BH3; [2] H2O2/HO- 
C)  H2O, H2SO4 
D)  [1] BH3; [2] H2O 
A)  H2O, Br2 
B)  [1] BH3; [2] H2O2/HO- 
C)  H2O, H2SO4 
D)  [1] BH3; [2] H2O B

Question 3

Which of the following reactions of alkenes takes place with anti stereochemistry only?

Accepted Answer

A)  Addition of HBr 
B)  Addition of H2O in the presence of H2SO4 
C)  Addition of BH3 followed by H2O2/HO- 
D)  Addition of Br2 
A)  Addition of HBr 
B)  Addition of H2O in the presence of H2SO4 
C)  Addition of BH3 followed by H2O2/HO- 
D)  Addition of Br2 D

Question 4

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 5

Which of the following alkenes will undergo a carbocation rearrangement when reacting with H2O in the presence of a small amount of H2SO4?

Accepted Answer

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

Question 6

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 7

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 8

Which of the following is a terpene?

Accepted Answer

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

Question 9

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 the above. 
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 the above.

Question 10

Predict the product of the following reaction.

Accepted Answer

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

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

Rank the following isomers in order of increasing boiling point, putting the least first.

Accepted Answer

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

Question 13

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 14

Which of the following compounds has the highest boiling point?

Accepted Answer

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

Question 15

Calculate the degree of unsaturation for a molecule with molecular formula C6H11Cl.

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  0 
A)  1 
B)  2 
C)  3 
D)  0

Question 16

Predict the major product(s) of the following reaction.

Accepted Answer

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

Question 17

Label each C-C double bond in Kavain, a naturally occurring relaxant, as E or Z.

Accepted Answer

A)  I = Z and II = Z 
B)  I = Z and II = E 
C)  I = E and II = E 
D)  I = E and II = Z 
A)  I = Z and II = Z 
B)  I = Z and II = E 
C)  I = E and II = E 
D)  I = E and II = Z

Question 18

Which of the following statements about the stereochemistry of electrophilic addition of HX to alkenes is true?

Accepted Answer

A)  Achiral starting materials yield an unequal mixture of two enantiomers. 
B)  Hydrohalogenation occurs with syn stereochemistry only. 
C)  Hydrohalogenation occurs with anti stereochemistry only. 
D)  Hydrohalogenation occurs with syn and anti addition of HX. 
A)  Achiral starting materials yield an unequal mixture of two enantiomers. 
B)  Hydrohalogenation occurs with syn stereochemistry only. 
C)  Hydrohalogenation occurs with anti stereochemistry only. 
D)  Hydrohalogenation occurs with syn and anti addition of HX.

Question 19

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 20

What is the major product obtained from the following reaction (assume enantiomer is also formed)?

Accepted Answer

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

Exam 10: Alkenes

What is the major product obtained from the following reaction?

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

Which of the following reactions of alkenes takes place with anti stereochemistry only?

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

Which of the following alkenes will undergo a carbocation rearrangement when reacting with H2O in the presence of a small amount of H2SO4?

Predict the major product of the following reaction.

What is the IUPAC name for the following compound?

Which of the following is a terpene?

Rearrangements can occur in which of the following reactions?

Predict the product of the following reaction.

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

Rank the following isomers in order of increasing boiling point, putting the least first.

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

Which of the following compounds has the highest boiling point?

Calculate the degree of unsaturation for a molecule with molecular formula C6H11Cl.

Predict the major product(s) of the following reaction.

Label each C-C double bond in Kavain, a naturally occurring relaxant, as E or Z.

Which of the following statements about the stereochemistry of electrophilic addition of HX to alkenes is true?

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

What is the major product obtained from the following reaction (assume enantiomer is also formed)?

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

Which of the following alkenes will undergo a carbocation rearrangement when reacting with H₂O in the presence of a small amount of H₂SO₄?

Calculate the degree of unsaturation for a molecule with molecular formula C₆H₁₁Cl.