Question 1

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 B

Question 2

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 A

Question 3

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. A

Question 4

Calculate the degree of unsaturation for the following molecule:

Accepted Answer

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

Question 5

Calculate the degree of unsaturation for the following molecule:

Accepted Answer

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

Question 6

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 7

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 8

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 9

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 10

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 11

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 12

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

Question 13

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 14

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

Question 15

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 16

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 17

Which alkene reacts fastest with HBr?

Accepted Answer

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

Question 18

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 19

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 20

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

Exam 10: Alkenes and Addition Reactions

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

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

Which of the following statements about alkenes is not true?

Calculate the degree of unsaturation for the following molecule:

Calculate the degree of unsaturation for the following molecule:

Predict the product of the following reaction.

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

Which of the following alkenes are terminal alkenes?

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

Which of the following alkenes are internal alkenes?

What is the IUPAC name for the following compound?

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

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

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

Rearrangements can occur in which of the following reactions?

Which of the following compounds has the highest boiling point?

Which alkene reacts fastest with HBr?

What is the major product of the following reaction?

What is the IUPAC name for the following compound?

Predict the major product of the following reaction.

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 and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

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