Question 1

What would be the optimal conditions to effect the following transformation?

Accepted Answer

A)  Dilute H2SO4 
B)  Concentrated H2SO4 
C)  Dilute HBr 
D)  Concentrated HBr 
A)  Dilute H2SO4 
B)  Concentrated H2SO4 
C)  Dilute HBr 
D)  Concentrated HBr

Question 2

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 3

The reaction shown below would be expected to produce as major products which of the following compounds?

Accepted Answer

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

Question 4

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

Accepted Answer

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

Question 5

What is the major product for the following reaction?

Accepted Answer

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

Question 6

Addition of HI to the alkene of the cyclobutane in the scheme below, results in a significant yield of the product shown. What other product(s) might also be obtained? Explain with a mechanism and brief discussion the observation of the given product as well as others that may arise.

Accepted Answer

@#IMG-DLM& Regioselective addition of the proton o

Question 7

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 8

Which of the following alkene addition reactions occur(s) specifically in syn fashion?

Accepted Answer

A)  dihydroxylation using OsO4, H2O2 
B)  addition of H2 
C)  hydroboration 
D)  addition of HCl 
E)  A, B, and C 
A)  dihydroxylation using OsO4, H2O2 
B)  addition of H2 
C)  hydroboration 
D)  addition of HCl 
E)  A, B, and C

Question 9

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 10

Predict the structure(s) of the expected major organic product(s) of the following reaction. Include regiochemical and/or stereochemical details as needed.

Accepted Answer

@#IMG-DLM& The reaction takes place with

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

What are the expected major products from 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 13

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 14

Which reaction is not stereospecific?

Accepted Answer

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

Question 15

How many distinct resonances would appear in the (proton-decoupled) 13C NMR spectrum for the product of the following reaction?

Accepted Answer

A)  4 
B)  5 
C)  6 
D)  7 
A)  4 
B)  5 
C)  6 
D)  7

Question 16

For an addition reaction, why does free energy, $\Delta$ G, become more positive with increasing temperature?

Accepted Answer

A)  The positive entropy dominates at high temperature. 
B)  The negative entropy dominates at high temperature. 
C)  The positive enthalpy dominates at high temperature. 
D)  The negative enthalpy dominates at high temperature. 
E)  The enthalpy and entropy cancel at high temperature. 
A)  The positive entropy dominates at high temperature. 
B)  The negative entropy dominates at high temperature. 
C)  The positive enthalpy dominates at high temperature. 
D)  The negative enthalpy dominates at high temperature. 
E)  The enthalpy and entropy cancel at high temperature.

Question 17

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 18

The expected major product of the following reaction is:

Accepted Answer

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

Question 19

The regioselectivity and stereospecificity in the acid-catalyzed hydration of an alkene is best described as:

Accepted Answer

A)  Markovnikov orientation with syn-addition 
B)  Markovnikov orientation with anti-addition 
C)  anti-Markovnikov orientation with syn-addition 
D)  anti-Markovnikov orientation with anti-addition 
E)  Markovnikov orientation with both syn- and anti-addition 
A)  Markovnikov orientation with syn-addition 
B)  Markovnikov orientation with anti-addition 
C)  anti-Markovnikov orientation with syn-addition 
D)  anti-Markovnikov orientation with anti-addition 
E)  Markovnikov orientation with both syn- and anti-addition

Question 20

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

Accepted Answer

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

Exam 9: Addition Reactions of Alkenes

What would be the optimal conditions to effect the following transformation?

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

The reaction shown below would be expected to produce as major products which of the following compounds?

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

What is the major product for the following reaction?

Addition of HI to the alkene of the cyclobutane in the scheme below, results in a significant yield of the product shown. What other product(s) might also be obtained? Explain with a mechanism and brief discussion the observation of the given product as well as others that may arise.

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

Which of the following alkene addition reactions occur(s) specifically in syn fashion?

Addition reactions of alkenes are characterized by:

Predict the structure(s) of the expected major organic product(s) of the following reaction. Include regiochemical and/or stereochemical details as needed.

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

What are the expected major products from the reaction sequence shown below?

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

Which reaction is not stereospecific?

How many distinct resonances would appear in the (proton-decoupled) 13C NMR spectrum for the product of the following reaction?

For an addition reaction, why does free energy, Δ\DeltaΔ G, become more positive with increasing temperature?

The expected major product of the following reaction is:

The expected major product of the following reaction is:

The regioselectivity and stereospecificity in the acid-catalyzed hydration of an alkene is best described as:

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

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

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

How many distinct resonances would appear in the (proton-decoupled) ¹³C NMR spectrum for the product of the following reaction?

For an addition reaction, why does free energy, $\Delta$ G, become more positive with increasing temperature?