Question 1

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

Accepted Answer

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

Question 2

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 3

Which of the given reaction schemes would produce the molecule shown below?

Accepted Answer

A)    
B)    
C)    
D)  Both A and B 
E)  Both B and C 
A)    
B)    
C)    
D)  Both A and B 
E)  Both B and C

Question 4

To accomplish a Markovnikov addition of water to an unsymmetrical alkene with minimal skeletal rearrangement, the best reagents would be:

Accepted Answer

A)  water and dilute acid 
B)  water and concentrated acid 
C)  1. Hg(OAc)2, H2O 2. NaBH4, NaOH 
D)  1. BH3•THF 2. H2O2, NaOH 
E)  1. OsO4, pyridine 2. NaHSO3, H2O 
A)  water and dilute acid 
B)  water and concentrated acid 
C)  1. Hg(OAc)2, H2O 2. NaBH4, NaOH 
D)  1. BH3•THF 2. H2O2, NaOH 
E)  1. OsO4, pyridine 2. NaHSO3, H2O

Question 5

Treatment of 1-methylcyclohexene with H3O+ would be expected to yield as the major product which of the molecules below?

Accepted Answer

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

Question 6

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

Accepted Answer

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

Question 7

What is the name of the product formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H2?

Accepted Answer

A)  1-chloro-2-methylcyclohexane 
B)  1-chloro-3-methylcyclohexane 
C)  1-chloro-5-methylcyclohexane 
D)  3-chloro-1-methylcyclohexane 
E)  None of the above 
A)  1-chloro-2-methylcyclohexane 
B)  1-chloro-3-methylcyclohexane 
C)  1-chloro-5-methylcyclohexane 
D)  3-chloro-1-methylcyclohexane 
E)  None of the above

Question 8

The expected major product of the following reaction is:

Accepted Answer

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

Question 9

Which of the following compounds would react most rapidly with a dilute aqueous solution of H2SO4?

Accepted Answer

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

Question 10

Which of the molecules below arises from anti-Markovnikov hydrohalogenation with HBr of the alkene shown?

Accepted Answer

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

Question 11

Which of the molecules below would be the expected product for hydrohalogenation of the following alkene with HBr:

Accepted Answer

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

Question 12

The expected major product of the following reaction is:

Accepted Answer

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

Question 13

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and catalytic OsO4 with NMO.

Accepted Answer

@#IMG-DLM& The reaction takes

Question 14

What is the expected major product for the following reaction?

Accepted Answer

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

Question 15

Which of the statements is most correct regarding the products expected from the halogenation reaction shown below?

Accepted Answer

A)  Equal amounts of I and II are produced. 
B)  Equal amounts of III and IV are produced. 
C)  Equal amounts of I and IV are produced. 
D)  Equal amounts of II and III are produced. 
E)  Equal amounts of I and III are produced. 
A)  Equal amounts of I and II are produced. 
B)  Equal amounts of III and IV are produced. 
C)  Equal amounts of I and IV are produced. 
D)  Equal amounts of II and III are produced. 
E)  Equal amounts of I and III are produced.

Question 16

The expected Markovnikov addition product of HI to 2-methyl-2-butene is:

Accepted Answer

A)  2-iodopentane 
B)  2-iodo-2-methylbutane 
C)  1-iodo-2-methylbutane 
D)  1-iodo-3-methylbutane 
E)  2-iodo-3-methylbutane 
A)  2-iodopentane 
B)  2-iodo-2-methylbutane 
C)  1-iodo-2-methylbutane 
D)  1-iodo-3-methylbutane 
E)  2-iodo-3-methylbutane

Question 17

The decrease in entropy (the $\Delta$S value is negative) observed for alkene addition reactions results from:

Accepted Answer

A)  the breaking of a π and $\sigma$ bond. 
B)  the formation of two $\sigma$ bonds. 
C)  the reaction being exothermic. 
D)  two molecules reacting to form a single molecule. 
E)  the temperature dependence of the $\Delta$S term. 
A)  the breaking of a π and $\sigma$ bond. 
B)  the formation of two $\sigma$ bonds. 
C)  the reaction being exothermic. 
D)  two molecules reacting to form a single molecule. 
E)  the temperature dependence of the $\Delta$S term.

Question 18

Identify the expected major organic product generated from the reaction sequence shown.

Accepted Answer

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

Question 19

In a reaction where addition and elimination reactions are in equilibrium, which of the following statements is most correct?

Accepted Answer

A)  Addition and elimination reactions are favored at low temperatures. 
B)  Addition and elimination reactions are favored at high temperatures. 
C)  Only addition reactions are favored at low temperatures. 
D)  Only elimination reactions are favored at low temperatures. 
E)  Addition and elimination reactions are disfavored at low temperatures. 
A)  Addition and elimination reactions are favored at low temperatures. 
B)  Addition and elimination reactions are favored at high temperatures. 
C)  Only addition reactions are favored at low temperatures. 
D)  Only elimination reactions are favored at low temperatures. 
E)  Addition and elimination reactions are disfavored at low temperatures.

Question 20

An unknown alkene was reacted with MCPBA in dichloromethane, followed by work-up with H2O/H+. A racemic mixture of the compound shown below was obtained. What is correct name of the starting alkene?

Accepted Answer

A)  (Z)-3-methylpent-2-ene 
B)  (
E) -3-methylpent-2-ene 
C)  2-methylpent-2-ene 
D)  2,3-dimethylbut-2-ene 
E)  none of the above 
A)  (Z)-3-methylpent-2-ene 
B)  (
E) -3-methylpent-2-ene 
C)  2-methylpent-2-ene 
D)  2,3-dimethylbut-2-ene 
E)  none of the above

Exam 9: Addition Reactions of Alkenes

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

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

Which of the given reaction schemes would produce the molecule shown below?

To accomplish a Markovnikov addition of water to an unsymmetrical alkene with minimal skeletal rearrangement, the best reagents would be:

Treatment of 1-methylcyclohexene with H3O+ would be expected to yield as the major product which of the molecules below?

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

What is the name of the product formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H2?

The expected major product of the following reaction is:

Which of the following compounds would react most rapidly with a dilute aqueous solution of H2SO4?

Which of the molecules below arises from anti-Markovnikov hydrohalogenation with HBr of the alkene shown?

Which of the molecules below would be the expected product for hydrohalogenation of the following alkene with HBr:

The expected major product of the following reaction is:

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and catalytic OsO4 with NMO.

What is the expected major product for the following reaction?

Which of the statements is most correct regarding the products expected from the halogenation reaction shown below?

The expected Markovnikov addition product of HI to 2-methyl-2-butene is:

The decrease in entropy (the Δ\DeltaΔ S value is negative) observed for alkene addition reactions results from:

Identify the expected major organic product generated from the reaction sequence shown.

In a reaction where addition and elimination reactions are in equilibrium, which of the following statements is most correct?

An unknown alkene was reacted with MCPBA in dichloromethane, followed by work-up with H2O/H+. A racemic mixture of the compound shown below was obtained. What is correct name of the starting alkene?

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

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Substitution Reactions

Alkenes: Structure and Preparation Via 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

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Treatment of 1-methylcyclohexene with H₃O⁺ would be expected to yield as the major product which of the molecules below?

What is the name of the product formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H₂?

Which of the following compounds would react most rapidly with a dilute aqueous solution of H₂SO₄?

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and catalytic OsO₄ with NMO.

The decrease in entropy (the $\Delta$ S value is negative) observed for alkene addition reactions results from:

An unknown alkene was reacted with MCPBA in dichloromethane, followed by work-up with H₂O/H⁺. A racemic mixture of the compound shown below was obtained. What is correct name of the starting alkene?