Question 1

When an alkene is subjected to treatment with Hg(OAc)2 in alcohol, followed by reaction with NaBH4, what functional group is formed?

Accepted Answer

A)  ether 
B)  epoxide 
C)  alkane 
D)  syn diol 
E)  alkyne 
A)  ether 
B)  epoxide 
C)  alkane 
D)  syn diol 
E)  alkyne

Question 2

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 3

For the catalytic hydrogenation of alkenes, select from below those most likely to function as a homogenous catalyst?

Accepted Answer

A)  Wilkinson's catalyst 
B)  Ni 
C)  Pd 
D)  Pt 
E)  Au 
A)  Wilkinson's catalyst 
B)  Ni 
C)  Pd 
D)  Pt 
E)  Au

Question 4

Identify the major organic product generated from the reaction shown.

Accepted Answer

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

Question 5

For the following dihydroxylation reaction which of the following statements is correct regarding the expected products?

Accepted Answer

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

Question 6

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

Question 7

The transformation shown below generates an achiral product from a chiral starting material. Provide the structure of the expected product and a mechanism explaining the transformation. Briefly explain why the product formed is achiral.

Accepted Answer

@#IMG-DLM& @#IMG-DLM& Upon addition of the proton to the alk

Question 8

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

Accepted Answer

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

Question 9

Which alkene would yield 3-methylpentane upon subjection to catalytic hydrogenation?

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 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 11

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

Accepted Answer

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

Question 12

What is (are) the expected major product(s) for the following reaction sequence?

Accepted Answer

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

Question 13

What reagents are needed to accomplish the following transformation?

Accepted Answer

A)  H2O/H+ 
B)  H2O/Peroxide 
C)  OH- 
D)  BH3.THF 
E)  1. BH3.THF, 2. HO-, H2O2, H2O 
A)  H2O/H+ 
B)  H2O/Peroxide 
C)  OH- 
D)  BH3.THF 
E)  1. BH3.THF, 2. HO-, H2O2, H2O

Question 14

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 15

A reaction that could potentially yield two or more constitutional isomers, but as in hydroboration-oxidation produces only one isomer, is said to be _____________________.

Accepted Answer

The answer of A reaction that could potentially yield two...

Question 16

The reaction of HCl with 2-ethyl-1-pentene or HCl with 3-methyl-2-hexene results in the identical major product of 3-chloro-3-methylhexane. Provide a mechanistic scheme showing the reaction of each alkene with HCl, including the intermediate and product. Provide a brief explanation how the different alkene reactants were transformed into the same product.

Accepted Answer

@#IMG-DLM& Electrophilic addition of a proton in t

Question 17

Identify the expected product(s) for the reaction shown below:

Accepted Answer

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

Question 18

For this question, the "entropy term" refers to "-TΔS". Addition reactions are generally favorable at low temperatures because:

Accepted Answer

A)  the positive enthalpy term is larger than the negative entropy term. 
B)  the negative enthalpy term is larger than the positive entropy term. 
C)  the positive enthalpy term is smaller than the negative entropy term. 
D)  the negative enthalpy term is smaller than the positive entropy term. 
E)  the enthalpy and entropy terms are equal. 
A)  the positive enthalpy term is larger than the negative entropy term. 
B)  the negative enthalpy term is larger than the positive entropy term. 
C)  the positive enthalpy term is smaller than the negative entropy term. 
D)  the negative enthalpy term is smaller than the positive entropy term. 
E)  the enthalpy and entropy terms are equal.

Question 19

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-2-methyl-3-hexene and cold, alkaline KMnO4.

Accepted Answer

@#IMG-DLM& The reaction takes

Question 20

What is the expected major product for the following reaction?

Accepted Answer

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

Exam 9: Addition Reactions of Alkenes

When an alkene is subjected to treatment with Hg(OAc)2 in alcohol, followed by reaction with NaBH4, what functional group is formed?

What is the expected major product for the following reaction?

For the catalytic hydrogenation of alkenes, select from below those most likely to function as a homogenous catalyst?

Identify the major organic product generated from the reaction shown.

For the following dihydroxylation reaction which of the following statements is correct regarding the expected products?

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

The transformation shown below generates an achiral product from a chiral starting material. Provide the structure of the expected product and a mechanism explaining the transformation. Briefly explain why the product formed is achiral.

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

Which alkene would yield 3-methylpentane upon subjection to catalytic hydrogenation?

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

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

What is (are) the expected major product(s) for the following reaction sequence?

What reagents are needed to accomplish the following transformation?

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

A reaction that could potentially yield two or more constitutional isomers, but as in hydroboration-oxidation produces only one isomer, is said to be _____________________.

Identify the expected product(s) for the reaction shown below:

For this question, the "entropy term" refers to "-TΔS". Addition reactions are generally favorable at low temperatures because:

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-2-methyl-3-hexene and cold, alkaline KMnO4.

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

When an alkene is subjected to treatment with Hg(OAc)₂ in alcohol, followed by reaction with NaBH₄, what functional group is formed?

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

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-2-methyl-3-hexene and cold, alkaline KMnO₄.