Question 1

Provide the reagents necessary to complete the following transformation.

Accepted Answer

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

Question 2

When isobutylene [CH2-C(CH3)2] is treated with BF3, polyisobutylene is formed. Provide a step-by-step mechanism for this polymerization reaction.

Accepted Answer

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 structure of the major organic product of the reaction below.

Accepted Answer

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

Question 5

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 6

Treatment of cyclopentene with peroxybenzoic acid ________.

Accepted Answer

A)  results in oxidative cleavage of the ring to produce an acyclic compound 
B)  yields a meso epoxide 
C)  yields an equimolar mixture of enantiomeric epoxides 
D)  gives the same product as treatment of cyclopentene with OsO4 
E)  none of the above 
A)  results in oxidative cleavage of the ring to produce an acyclic compound 
B)  yields a meso epoxide 
C)  yields an equimolar mixture of enantiomeric epoxides 
D)  gives the same product as treatment of cyclopentene with OsO4 
E)  none of the above

Question 7

Provide the major organic product of the reaction below.

Accepted Answer

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

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

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 11

Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

Accepted Answer

The answer of Complete the following reaction and provide a...

Question 12

Draw the major regioisomeric product generated in the reaction below.

Accepted Answer

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

Question 13

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 14

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 15

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 16

Which of the following steps would successfully complete the following reaction?

Accepted Answer

A)  I only 
B)  II & III 
C)  I & IV 
D)  I, II, & IV 
A)  I only 
B)  II & III 
C)  I & IV 
D)  I, II, & IV

Question 17

What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration sequence?

Accepted Answer

A)  Markovnikov addition of H2O wherein skeletal rearrangement is promoted 
B)  Markovnikov addition of H2O wherein skeletal rearrangement is prevented 
C)  anti-Markovnikov addition of H2O wherein skeletal rearrangement is promoted 
D)  anti-Markovnikov addition of H2O wherein skeletal rearrangement is prevented 
E)  syn-hydroxylation 
A)  Markovnikov addition of H2O wherein skeletal rearrangement is promoted 
B)  Markovnikov addition of H2O wherein skeletal rearrangement is prevented 
C)  anti-Markovnikov addition of H2O wherein skeletal rearrangement is promoted 
D)  anti-Markovnikov addition of H2O wherein skeletal rearrangement is prevented 
E)  syn-hydroxylation

Question 18

Provide the reagents necessary to complete the following transformation.

Accepted Answer

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

Question 19

Provide the reagents necessary to complete the following transformation.

Accepted Answer

1. Br₂, hν 2. H

Question 20

Ozonolysis-reduction of an unknown alkene gives equal amounts of CH3CH2CHO and CH3CH2CH2CHO. Name the unknown alkene.

Accepted Answer

Either (E)

Exam 8: Reactions of Alkenes

Provide the reagents necessary to complete the following transformation.

When isobutylene [CH2-C(CH3)2] is treated with BF3, polyisobutylene is formed. Provide a step-by-step mechanism for this polymerization reaction.

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.

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

Treatment of cyclopentene with peroxybenzoic acid ________.

Provide the major organic product of the reaction below.

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.

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

Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

Draw the major regioisomeric product generated in the reaction below.

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?

Which of the following steps would successfully complete the following reaction?

What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration sequence?

Provide the reagents necessary to complete the following transformation.

Provide the reagents necessary to complete the following transformation.

Ozonolysis-reduction of an unknown alkene gives equal amounts of CH3CH2CHO and CH3CH2CH2CHO. Name the unknown alkene.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Alkynes

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

When isobutylene [CH₂-C(CH₃)₂] is treated with BF₃, polyisobutylene is formed. Provide a step-by-step mechanism for this polymerization reaction.

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

Ozonolysis-reduction of an unknown alkene gives equal amounts of CH₃CH₂CHO and CH₃CH₂CH₂CHO. Name the unknown alkene.