Question 1

Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

Accepted Answer

A)  water + dilute acid 
B)  water + concentrated acid 
C)  oxymercuration-demercuration 
D)  hydroboration-oxidation 
E)  none of the above 
A)  water + dilute acid 
B)  water + concentrated acid 
C)  oxymercuration-demercuration 
D)  hydroboration-oxidation 
E)  none of the above

Question 2

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Accepted Answer

The answer of Draw the major organic product generated in...

Question 3

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Accepted Answer

The answer of Draw the major organic product generated in...

Question 4

Provide the reagents necessary to complete the following transformation.

Accepted Answer

A)  1. BH3∙THF 2. H2O2, HO- 
B)  H2O, H2SO4 
C)  OsO4, H2O2 
D)  CH3CO3H 
E)  1. CH3CO3H 2. H+, H2O 
A)  1. BH3∙THF 2. H2O2, HO- 
B)  H2O, H2SO4 
C)  OsO4, H2O2 
D)  CH3CO3H 
E)  1. CH3CO3H 2. H+, H2O

Question 5

Draw a mechanism that shows how the product is formed.

Accepted Answer

The answer of Draw a mechanism that shows how the...

Question 6

Complete the following reaction by filling in the appropriate reagents.

Accepted Answer

The answer of Complete the following reaction by filling in...

Question 7

Addition of Br2 to (E)-hex-3-ene produces ________.

Accepted Answer

A)  a meso dibromide 
B)  a mixture of enantiomeric dibromides which is optically active 
C)  a mixture of enantiomeric dibromides which is optically inactive 
D)  (Z)-3,4-dibromo-3-hexene 
E)  (
E) -3,4-dibromo-3-hexene 
A)  a meso dibromide 
B)  a mixture of enantiomeric dibromides which is optically active 
C)  a mixture of enantiomeric dibromides which is optically inactive 
D)  (Z)-3,4-dibromo-3-hexene 
E)  (
E) -3,4-dibromo-3-hexene

Question 8

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Accepted Answer

The answer of Draw the major organic product generated in...

Question 9

Provide the structure of the major organic product of the reaction below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 10

Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at room temperature?

Accepted Answer

A)    
B)    
C)    
D)    
E)  both Band D 
A)    
B)    
C)    
D)    
E)  both Band D

Question 11

Humulene is a monocyclic terpene constituent of carnations. When 0.25 mol of humulene is hydrogenated in the presence of platinum catalyst, 0.75 mol of H2 reacts with the humulene to produce a monocyclic hydrocarbon of formula C15H30. What is the molecular formula of humulene?

Accepted Answer

Question 12

Based on the relative stabilities of the intermediates involved, explain the basis for Markovinkov's rule in the addition of hydrogen halides to alkenes.

Accepted Answer

The rate-determining step in this reacti

Question 13

Provide the structure of the major organic product of the reaction below.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 14

Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Accepted Answer

The answer of Draw the major organic product(s) generated in...

Question 15

Provide the reagents necessary to complete the following transformation.

Accepted Answer

A)  1. BH3∙THF 2. H2O2, HO- 
B)  H2O, H2SO4 
C)  OsO4, H2O2 
D)  CH3CO3H 
E)  1. CH3CO3H 2. H+, H2O 
A)  1. BH3∙THF 2. H2O2, HO- 
B)  H2O, H2SO4 
C)  OsO4, H2O2 
D)  CH3CO3H 
E)  1. CH3CO3H 2. H+, H2O

Question 16

Draw a full and complete mechanism to account for the formation of the product in the reaction shown below.

Accepted Answer

The answer of Draw a full and complete mechanism to...

Question 17

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Accepted Answer

The answer of Draw the major organic product generated in...

Question 18

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Accepted Answer

The answer of Draw the major organic product generated in...

Question 19

Which one of these alkene would be likely to experience a carbocation rearrangement when treated with aqueous acid?

Accepted Answer

A)    
B)    
C)    
D)  None of these would undergo a rearrangement. 
A)    
B)    
C)    
D)  None of these would undergo a rearrangement.

Question 20

________ is the use of an optically active reagent or catalyst to convert an optically inactive starting material into an optically active product.

Accepted Answer

A)  Asymmetric induction 
B)  Racemization 
C)  Optical reduction 
D)  Meso effection 
E)  Chiralization 
A)  Asymmetric induction 
B)  Racemization 
C)  Optical reduction 
D)  Meso effection 
E)  Chiralization

Exam 8: Reactions of Alkenes

Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Provide the reagents necessary to complete the following transformation.

Draw a mechanism that shows how the product is formed.

Complete the following reaction by filling in the appropriate reagents.

Addition of Br2 to (E)-hex-3-ene produces ________.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Provide the structure of the major organic product of the reaction below.

Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at room temperature?

Humulene is a monocyclic terpene constituent of carnations. When 0.25 mol of humulene is hydrogenated in the presence of platinum catalyst, 0.75 mol of H2 reacts with the humulene to produce a monocyclic hydrocarbon of formula C15H30. What is the molecular formula of humulene?

Based on the relative stabilities of the intermediates involved, explain the basis for Markovinkov's rule in the addition of hydrogen halides to alkenes.

Provide the structure of the major organic product of the reaction below.

Draw the major organic product(s) generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Provide the reagents necessary to complete the following transformation.

Draw a full and complete mechanism to account for the formation of the product in the reaction shown below.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Draw the major organic product generated in the reaction below. Pay particular attention to regio- and stereochemical detail.

Which one of these alkene would be likely to experience a carbocation rearrangement when treated with aqueous acid?

________ is the use of an optically active reagent or catalyst to convert an optically inactive starting material into an optically active product.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Addition of Br₂ to (E)-hex-3-ene produces ________.

Which of the following alkenes will yield a meso dihalide when reacted with Br₂/CCl₄ at room temperature?

Humulene is a monocyclic terpene constituent of carnations. When 0.25 mol of humulene is hydrogenated in the presence of platinum catalyst, 0.75 mol of H₂ reacts with the humulene to produce a monocyclic hydrocarbon of formula C₁₅H₃₀. What is the molecular formula of humulene?