Question 1

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- D

Question 2

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 3

What is the IUPAC name of the following compound?

Accepted Answer

A) (E,R)-4-bromo-4-hexen-2-ol 
B) (Z,R)-4-bromo-4-hexen-2-ol 
C) (E,S)-4-bromo-4-hexen-2-ol 
D) (Z,S)-4-bromo-4-hexen-2-ol 
A) (E,R)-4-bromo-4-hexen-2-ol 
B) (Z,R)-4-bromo-4-hexen-2-ol 
C) (E,S)-4-bromo-4-hexen-2-ol 
D) (Z,S)-4-bromo-4-hexen-2-ol B

Question 4

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 5

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 6

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 7

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 8

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 9

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 10

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 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

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 13

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.

Question 14

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 15

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 16

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 17

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 18

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 19

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 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

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

What is the major product obtained from the following reaction?

What is the IUPAC name of the following compound?

Predict the product of the following reaction,ignoring stereochemistry.

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

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

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

What is the IUPAC name for the following compound?

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

Predict the major product of the following reaction.

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

Rearrangements can occur in which of the following reactions?

Which of the following statements about alkenes is not true?

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

Which of the following compounds has the highest boiling point?

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

What is the major product of 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.

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

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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

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