Question 1

What is the major product of the reaction below?

Accepted Answer

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

Question 2

Treatment of 1,2-dimethylcyclopentene with OsO4, followed by aqueous NaHSO3, produces which of the following?

Accepted Answer

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

Question 3

What is the expected major product upon reaction of 1-pentene with Cl2?

Accepted Answer

A)  1-chloropentane 
B)  2-chloropentane 
C)  1,1-dichloropentane 
D)  2,2-dichloropentane 
E)  1,2-dichloropentane 
A)  1-chloropentane 
B)  2-chloropentane 
C)  1,1-dichloropentane 
D)  2,2-dichloropentane 
E)  1,2-dichloropentane

Question 4

Which of the following carbocations is (are) likely to undergo rearrangement through a methyl shift?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  I and II 
E)  II and III 
A)  I 
B)  II 
C)  III 
D)  I and II 
E)  II and III

Question 5

What is the expected major product for 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 6

Which of the molecules below are enantiomers formed as products upon reaction of HBr with 4-methylpent-1-ene?

Accepted Answer

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

Question 7

Which of the following carbocations is (are) likely to undergo rearrangement through a hydride shift?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  I and II 
E)  II and III 
A)  I 
B)  II 
C)  III 
D)  I and II 
E)  II and III

Question 8

Which reaction intermediate is formed when 4?methylcyclohexene reacts with Br2 dissolved in CCl4?

Accepted Answer

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

Question 9

What is the expected major product for 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 10

Which of the alkenes below would be expected to produce at least one chirality center upon hydrohalogenation in the presence of peroxide?

Accepted Answer

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

Question 11

What is the expected major product of the following reaction sequence?

Accepted Answer

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

Question 12

What is the expected major product for the following reaction sequence?

Accepted Answer

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

Question 13

Addition reactions of alkenes are characterized by _________.

Accepted Answer

A)  formation of a π bond 
B)  addition of two groups across a double bond 
C)  breaking of a π bond 
D)  A and B 
E)  B and C 
A)  formation of a π bond 
B)  addition of two groups across a double bond 
C)  breaking of a π bond 
D)  A and B 
E)  B and C

Question 14

What product is formed when trans-1,2-dimethylcyclohexane is reacted with Pd/C and H2?

Accepted Answer

A)  No reaction 
B)  cis-1,2-dimethylcyclohexane 
C)  trans-3,4-dimethylhexane 
D)  trans-1,2-dimethylhexane 
E)  None of the above 
A)  No reaction 
B)  cis-1,2-dimethylcyclohexane 
C)  trans-3,4-dimethylhexane 
D)  trans-1,2-dimethylhexane 
E)  None of the above

Question 15

In conducting the catalytic hydrogenation of an alkene, which catalyst listed is most likely soluble in the reaction medium?

Accepted Answer

A)  Ni 
B)  Pt 
C)  Pd 
D)  Wilkinson's catalyst 
E)  All of the above are soluble 
A)  Ni 
B)  Pt 
C)  Pd 
D)  Wilkinson's catalyst 
E)  All of the above are soluble

Question 16

Give the expected major product of 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 17

Any proper mechanism of hydroboration-oxidation must explain the observed _________ addition of the H and OH to the alkene as well as the _____________ regiochemistry.

Accepted Answer

syn, anti-

Question 18

In the addition reaction of HI to 2-methyl-2-butene, what is the first step?

Accepted Answer

A)  attack of 2-methyl-2-butene initiated by an iodide ion 
B)  attack of 2-methyl-2-butene initiated by an iodine atom 
C)  isomerization of 2-iodo-2-methylbutene 
D)  formation of a carbocation at carbon two (C-2) 
E)  formation of carbocation at carbon three (C-3) 
A)  attack of 2-methyl-2-butene initiated by an iodide ion 
B)  attack of 2-methyl-2-butene initiated by an iodine atom 
C)  isomerization of 2-iodo-2-methylbutene 
D)  formation of a carbocation at carbon two (C-2) 
E)  formation of carbocation at carbon three (C-3)

Question 19

Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme.

Accepted Answer

The answer of Provide the structure(s) of the expected major...

Question 20

The three compounds below can form a carbocation under aqueous acidic conditions. Which ones will form the same carbocation?

Accepted Answer

A)  I and II 
B)  I and III 
C)  II and III 
D)  All three will form the same carbocation 
A)  I and II 
B)  I and III 
C)  II and III 
D)  All three will form the same carbocation

Exam 8: Addition Reactions of Alkenes

What is the major product of the reaction below?

Treatment of 1,2-dimethylcyclopentene with OsO4, followed by aqueous NaHSO3, produces which of the following?

What is the expected major product upon reaction of 1-pentene with Cl2?

Which of the following carbocations is (are) likely to undergo rearrangement through a methyl shift?

What is the expected major product for the following reaction?

Which of the molecules below are enantiomers formed as products upon reaction of HBr with 4-methylpent-1-ene?

Which of the following carbocations is (are) likely to undergo rearrangement through a hydride shift?

Which reaction intermediate is formed when 4?methylcyclohexene reacts with Br2 dissolved in CCl4?

What is the expected major product for the following reaction?

Which of the alkenes below would be expected to produce at least one chirality center upon hydrohalogenation in the presence of peroxide?

What is the expected major product of the following reaction sequence?

What is the expected major product for the following reaction sequence?

Addition reactions of alkenes are characterized by _________.

What product is formed when trans-1,2-dimethylcyclohexane is reacted with Pd/C and H2?

In conducting the catalytic hydrogenation of an alkene, which catalyst listed is most likely soluble in the reaction medium?

Give the expected major product of the following reaction.

Any proper mechanism of hydroboration-oxidation must explain the observed _________ addition of the H and OH to the alkene as well as the _____________ regiochemistry.

In the addition reaction of HI to 2-methyl-2-butene, what is the first step?

Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme.

The three compounds below can form a carbocation under aqueous acidic conditions. Which ones will form the same carbocation?

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Treatment of 1,2-dimethylcyclopentene with OsO₄, followed by aqueous NaHSO₃, produces which of the following?

What is the expected major product upon reaction of 1-pentene with Cl₂?

Which reaction intermediate is formed when 4?methylcyclohexene reacts with Br₂ dissolved in CCl₄?

What product is formed when trans-1,2-dimethylcyclohexane is reacted with Pd/C and H₂?

Any proper mechanism of hydroboration-oxidation must explain the observed _ addition of the H and OH to the alkene as well as the _____ regiochemistry.