Question 1

Consider the ozonolysis products obtained from all the unbranched and unsymmetrical isomers of heptene.The reaction product in each case would consist of:

Accepted Answer

A) a single aldehyde. 
B) an aldehyde and a ketone. 
C) two different ketones. 
D) two different aldehydes. 
E) a single ketone. 
A) a single aldehyde. 
B) an aldehyde and a ketone. 
C) two different ketones. 
D) two different aldehydes. 
E) a single ketone.

Question 2

Hydroboration-oxidation is a reaction with ___ stereochemistry and ___ regiochemistry.

Accepted Answer

syn,anti-M

Question 3

What is the major product for the following reaction?

Accepted Answer

A)    
B)    
C)    
D)    
E) More than one of these choices. 
A)    
B)    
C)    
D)    
E) More than one of these choices.

Question 4

Which of these compounds belongs to the class of substances commonly known as "halohydrins"?

Accepted Answer

A) BrCH2CH2Cl 
B) ClCH2CO2H 
C) ICH2CH2OH 
D) FCH2CH2NH2 
E) HOCH2 COCl 
A) BrCH2CH2Cl 
B) ClCH2CO2H 
C) ICH2CH2OH 
D) FCH2CH2NH2 
E) HOCH2 COCl

Question 5

Addition of hydrogen chloride to the following molecule would produce:

Accepted Answer

A) I and II 
B) II and III 
C) I and IV 
D) V 
E) All of these choices are equally likely to be formed. 
A) I and II 
B) II and III 
C) I and IV 
D) V 
E) All of these choices are equally likely to be formed.

Question 6

Which reaction of an alkene proceeds with anti addition?

Accepted Answer

A) Hydroboration/oxidation 
B) Bromination 
C) Oxidation with cold KMnO4 
D) Hydrogenation 
E) Oxymercuration-demercuration 
A) Hydroboration/oxidation 
B) Bromination 
C) Oxidation with cold KMnO4 
D) Hydrogenation 
E) Oxymercuration-demercuration

Question 7

Acid-catalyzed hydration of 2-methyl-1-butene would yield which of the following?

Accepted Answer

A) (CH3)2C(OH)CH2CH3 
B) CH2OHCH(CH3)CH2CH3 
C) (CH3)2CHCHOHCH3 
D) (CH3)2CHCH2CH2OH 
E) CH3CH2CH(CH3)CH2OH 
A) (CH3)2C(OH)CH2CH3 
B) CH2OHCH(CH3)CH2CH3 
C) (CH3)2CHCHOHCH3 
D) (CH3)2CHCH2CH2OH 
E) CH3CH2CH(CH3)CH2OH

Question 8

Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane.Molecules of the product would:

Accepted Answer

A) be a racemic form and,in their most stable conformation,they would have both bromine atoms equatorial. 
B) be a racemic form and,in their most stable conformation,they would have one bromine atom equatorial and one axial. 
C) be a meso compound and,in its most stable conformation,it would have both bromine atoms equatorial. 
D) be a meso compound and,in its most stable conformation,it would have one bromine atom equatorial and one axial. 
E) be a pair of diastereomers and,in their most stable conformation,one would have the bromines equatorial and axial,and the other would have the bromines equatorial and equatorial. 
A) be a racemic form and,in their most stable conformation,they would have both bromine atoms equatorial. 
B) be a racemic form and,in their most stable conformation,they would have one bromine atom equatorial and one axial. 
C) be a meso compound and,in its most stable conformation,it would have both bromine atoms equatorial. 
D) be a meso compound and,in its most stable conformation,it would have one bromine atom equatorial and one axial. 
E) be a pair of diastereomers and,in their most stable conformation,one would have the bromines equatorial and axial,and the other would have the bromines equatorial and equatorial.

Question 9

Which of the following reactions would yield the final product as a racemic form?

Accepted Answer

A) Cyclohexene + Br2,H2O 
B) Cyclohexene + cold,dilute KMnO4 and OH- 
C) Cyclohexene + HCl 
D) Cyclohexene + OsO4,then NaHSO3 
E) Cyclohexene + D2/Pt 
A) Cyclohexene + Br2,H2O 
B) Cyclohexene + cold,dilute KMnO4 and OH- 
C) Cyclohexene + HCl 
D) Cyclohexene + OsO4,then NaHSO3 
E) Cyclohexene + D2/Pt

Question 10

Which substance would undergo the following reaction?

Accepted Answer

A) 4-Hexen-1-yne R 
B) 3-methyl-1-hexene 
C) (
E) -2-hexene 
D) (Z)-2-hexene 
E) 4-methyl-1-pentene 
A) 4-Hexen-1-yne R 
B) 3-methyl-1-hexene 
C) (
E) -2-hexene 
D) (Z)-2-hexene 
E) 4-methyl-1-pentene

Question 11

Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product?

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 12

What is the major product of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) More than one of these choices. 
A)    
B)    
C)    
D)    
E) More than one of these choices.

Question 13

What is the final product of the following synthesis?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) An equimolar mixture of III and IV. 
A) I 
B) II 
C) III 
D) IV 
E) An equimolar mixture of III and IV.

Question 14

The reason why anti-Markovnikov addition is seen in the hydration of alkenes using hydroboration-oxidation conditions is due to steric interactions with the boron group attaching to the less substituted carbon more easily.

Accepted Answer

A) True 
 B)False

Question 15

Which reaction would give a meso compound as the product?

Accepted Answer

A) Cyclopentene + Br2/CCl4 
B) Cyclopentene + OsO4,then NaHSO3 
C) Cyclopentene + H3O+ 
D) Cyclopentene + Cl2,H2O 
E) More than one of these choices. 
A) Cyclopentene + Br2/CCl4 
B) Cyclopentene + OsO4,then NaHSO3 
C) Cyclopentene + H3O+ 
D) Cyclopentene + Cl2,H2O 
E) More than one of these choices.

Question 16

What is the major product of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) More than one of these choices. 
A)    
B)    
C)    
D)    
E) More than one of these choices.

Question 17

What is the major product of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) More than one of these choices. 
A)    
B)    
C)    
D)    
E) More than one of these choices.

Question 18

Which reaction is regioselective?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) None of these choices.

Question 19

Which product would you expect from the following reaction?

Accepted Answer

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

Question 20

What is the major product of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Exam 8: Alkenes and Alkynes II

Consider the ozonolysis products obtained from all the unbranched and unsymmetrical isomers of heptene.The reaction product in each case would consist of:

Hydroboration-oxidation is a reaction with ___ stereochemistry and ___ regiochemistry.

What is the major product for the following reaction?

Which of these compounds belongs to the class of substances commonly known as "halohydrins"?

Addition of hydrogen chloride to the following molecule would produce:

Which reaction of an alkene proceeds with anti addition?

Acid-catalyzed hydration of 2-methyl-1-butene would yield which of the following?

Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane.Molecules of the product would:

Which of the following reactions would yield the final product as a racemic form?

Which substance would undergo the following reaction?

Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product?

What is the major product of the following reaction sequence?

What is the final product of the following synthesis?

The reason why anti-Markovnikov addition is seen in the hydration of alkenes using hydroboration-oxidation conditions is due to steric interactions with the boron group attaching to the less substituted carbon more easily.

Which reaction would give a meso compound as the product?

What is the major product of the following reaction sequence?

What is the major product of the following reaction sequence?

Which reaction is regioselective?

Which product would you expect from the following reaction?

What is the major product of the following reaction sequence?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Hydroboration-oxidation is a reaction with _ stereochemistry and _ regiochemistry.