Question 1

Which of the following sets of reagents accomplishes the transformation shown below?

Accepted Answer

A)  H2/HCl 
B)  H2/H2SO4 
C)  H2/Ni 
D)  H2O/Ni 
E)  H2O/H2SO4 
A)  H2/HCl 
B)  H2/H2SO4 
C)  H2/Ni 
D)  H2O/Ni 
E)  H2O/H2SO4 C

Question 2

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 A

Question 3

In an addition reaction to an alkene, the π bond plays the role of:

Accepted Answer

A)  nucleophile 
B)  electrophile 
C)  leaving group 
D)  A and B 
E)  B and C 
A)  nucleophile 
B)  electrophile 
C)  leaving group 
D)  A and B 
E)  B and C A

Question 4

What compound is the expected product upon Markovnikov hydrohalogenation with HBr of the alkene shown below?

Accepted Answer

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

Question 5

What is the expected major product of the reaction sequence shown below?

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 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 7

Which of the alkenes shown below would produce a chirality center upon Markovnikov hydrohalogenation?

Accepted Answer

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

Question 8

What is the expected major product resulting from the acid-catalyzed hydration of 2,5-dimethyl-2-hexene?

Accepted Answer

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

Question 9

When the two constitutional isomers, 3,3-dimethyl-1-butene and 2,3-dimethyl-2-butene, are reacted with HCl the same major product is formed. Provide a explanation for the observation.

Accepted Answer

@#IMG-DLM& For the unsymmetrical 3,3-dimethyl-1-bu

Question 10

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 11

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

Accepted Answer

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

Question 12

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 13

For the following reaction sequence, which molecule is expected as the major product?   
A)
   
B)
   
C)
   
D)
   
E)

Accepted Answer

A + its di

Question 14

For the following reaction sequence provide the expected major organic product(s). Include all stereoisomers showing relevant stereochemistry.

Accepted Answer

The answer of For the following reaction sequence provide the...

Question 15

In the addition reaction of HI to 2-methyl-2-butene, the Markovnikov addition mechanism involves:

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 16

Which of the following reagents effectively cleaves both the sigma and pi bonds of a carbon-carbon double bond?

Accepted Answer

A)  Cl2/hυ 
B)    
C)  H2SO4 
D)  cold KMnO4 
E)  1. O3 2. DMS 
A)  Cl2/hυ 
B)    
C)  H2SO4 
D)  cold KMnO4 
E)  1. O3 2. DMS

Question 17

For the reaction sequence below, identify the expected major product(s).

Accepted Answer

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

Question 18

The Markovnikov product resulting from an addition reaction to an unsymmetrical alkene is formed because:

Accepted Answer

A)  the product is statistically favored. 
B)  steric hindrance favors its formation. 
C)  the reaction proceeds via the more/most stable carbocation. 
D)  the reaction forms the more/most stable product. 
E)  All of the above are valid reasons 
A)  the product is statistically favored. 
B)  steric hindrance favors its formation. 
C)  the reaction proceeds via the more/most stable carbocation. 
D)  the reaction forms the more/most stable product. 
E)  All of the above are valid reasons

Question 19

Which of the following correctly describes the product(s) of the reaction below?

Accepted Answer

A)  Only one stereoisomer 
B)  An equal mixture of enantiomers 
C)  A roughly equal mixture of diasteromers 
D)  A roughly equal mixture of constitutional isomers 
A)  Only one stereoisomer 
B)  An equal mixture of enantiomers 
C)  A roughly equal mixture of diasteromers 
D)  A roughly equal mixture of constitutional isomers

Question 20

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

Exam 9: Addition Reactions of Alkenes

Which of the following sets of reagents accomplishes the transformation shown below?

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

In an addition reaction to an alkene, the π bond plays the role of:

What compound is the expected product upon Markovnikov hydrohalogenation with HBr of the alkene shown below?

What is the expected major product of the reaction sequence shown below?

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

Which of the alkenes shown below would produce a chirality center upon Markovnikov hydrohalogenation?

What is the expected major product resulting from the acid-catalyzed hydration of 2,5-dimethyl-2-hexene?

When the two constitutional isomers, 3,3-dimethyl-1-butene and 2,3-dimethyl-2-butene, are reacted with HCl the same major product is formed. Provide a explanation for the observation.

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

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

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

For the following reaction sequence, which molecule is expected as the major product? A) B) C) D) E)

For the following reaction sequence provide the expected major organic product(s). Include all stereoisomers showing relevant stereochemistry.

In the addition reaction of HI to 2-methyl-2-butene, the Markovnikov addition mechanism involves:

Which of the following reagents effectively cleaves both the sigma and pi bonds of a carbon-carbon double bond?

For the reaction sequence below, identify the expected major product(s).

The Markovnikov product resulting from an addition reaction to an unsymmetrical alkene is formed because:

Which of the following correctly describes the product(s) of the reaction below?

What is the expected major product for the following reaction?

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

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