Question 1

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

Accepted Answer

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

Question 2

Identify the expected major product of 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 C

Question 3

Identify the best reagents to accomplish a Markovnikov addition of water to an unsymmetrical alkene with minimal skeletal rearrangement.

Accepted Answer

A)  water and dilute acid 
B)  water and concentrated acid 
C)  1. Hg(OAc)2, H2O 2. NaBH4, NaOH 
D)  1. BH3•THF 2. H2O2, NaOH 
E)  1. OsO4, pyridine 2. NaHSO3, H2O 
A)  water and dilute acid 
B)  water and concentrated acid 
C)  1. Hg(OAc)2, H2O 2. NaBH4, NaOH 
D)  1. BH3•THF 2. H2O2, NaOH 
E)  1. OsO4, pyridine 2. NaHSO3, H2O C

Question 4

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 5

What is the expected major product resulting from treatment of (E)-3-methyl-3-hexene with Br2 in the presence of methanol, CH3OH?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above are produced in equal amounts 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above are produced in equal amounts

Question 6

Identify Wilkinson's catalyst.

Accepted Answer

A)  (Ph3P)3RhCl 
B)  (Ph3P)3RhBr 
C)  (Ph3P)3PbCl 
D)  (Ph3P)3PbBrl 
E)  (Ph3P)3RuCl 
A)  (Ph3P)3RhCl 
B)  (Ph3P)3RhBr 
C)  (Ph3P)3PbCl 
D)  (Ph3P)3PbBrl 
E)  (Ph3P)3RuCl

Question 7

An unknown alkene was reacted with MCPBA in dichloromethane, followed by work-up with H2O/H+. A racemic mixture of the compound shown below was obtained. What is correct name of the starting alkene?

Accepted Answer

A)  (Z)-3-methylpent-2-ene 
B)  (
E) -3-methylpent-2-ene 
C)  2-methylpent-2-ene 
D)  2,3-dimethylbut-2-ene 
E)  none of the above 
A)  (Z)-3-methylpent-2-ene 
B)  (
E) -3-methylpent-2-ene 
C)  2-methylpent-2-ene 
D)  2,3-dimethylbut-2-ene 
E)  none of the above

Question 8

The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is named after which chemist?

Accepted Answer

Vladimir M

Question 9

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

Accepted Answer

A)  3 
B)  4 
C)  5 
D)  6 
A)  3 
B)  4 
C)  5 
D)  6

Question 10

Provide the expected major organic product of the reaction sequence shown.

Accepted Answer

A)  I and II 
B)  IV and V 
C)  I only 
D)  II only 
E)  III only 
A)  I and II 
B)  IV and V 
C)  I only 
D)  II only 
E)  III only

Question 11

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 12

What is the 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 13

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 14

What are the expected major product(s) of HBr addition to the alkene 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 15

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

Accepted Answer

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

Question 16

Draw Fischer projections of the major product of the reaction between (Z)?2?methyl-3-hexene and aqueous Br2.

Accepted Answer

@#IMG-DLM&_TB4454_00 The reaction takes place with

Question 17

What is the expected major product of 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 18

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

Accepted Answer

A)  hydroboration-oxidation 
B)  addition of Br2 
C)  addition of H2 
D)  addition of H2O in dilute acid 
E)  both A and B 
A)  hydroboration-oxidation 
B)  addition of Br2 
C)  addition of H2 
D)  addition of H2O in dilute acid 
E)  both A and B

Question 19

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 20

Which statement best describes the temperature dependence of an addition reaction?

Accepted Answer

A)  Addition reactions are thermodynamically favored at all temperatures. 
B)  Addition reactions are thermodynamically disfavored at all temperatures. 
C)  Addition reactions are thermodynamically favored at low temperatures. 
D)  Addition reactions are thermodynamically favored at high temperatures. 
E)  Addition reactions are thermodynamically impossible. 
A)  Addition reactions are thermodynamically favored at all temperatures. 
B)  Addition reactions are thermodynamically disfavored at all temperatures. 
C)  Addition reactions are thermodynamically favored at low temperatures. 
D)  Addition reactions are thermodynamically favored at high temperatures. 
E)  Addition reactions are thermodynamically impossible.

Exam 8: Addition Reactions of Alkenes

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

Identify the expected major product of the following reaction.

Identify the best reagents to accomplish a Markovnikov addition of water to an unsymmetrical alkene with minimal skeletal rearrangement.

What is the expected major product for the following reaction?

What is the expected major product resulting from treatment of (E)-3-methyl-3-hexene with Br2 in the presence of methanol, CH3OH?

Identify Wilkinson's catalyst.

An unknown alkene was reacted with MCPBA in dichloromethane, followed by work-up with H2O/H+. A racemic mixture of the compound shown below was obtained. What is correct name of the starting alkene?

The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is named after which chemist?

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

Provide the expected major organic product of the reaction sequence shown.

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

What is the major product for the following reaction?

What is the expected major product for the following reaction?

What are the expected major product(s) of HBr addition to the alkene shown below?

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

Draw Fischer projections of the major product of the reaction between (Z)?2?methyl-3-hexene and aqueous Br2.

What is the expected major product of the following reaction?

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

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

Which statement best describes the temperature dependence of an addition reaction?

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and 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

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

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

What is the expected major product resulting from treatment of (E)-3-methyl-3-hexene with Br₂ in the presence of methanol, CH₃OH?

An unknown alkene was reacted with MCPBA in dichloromethane, followed by work-up with H₂O/H⁺. A racemic mixture of the compound shown below was obtained. What is correct name of the starting alkene?

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

Draw Fischer projections of the major product of the reaction between (Z)?2?methyl-3-hexene and aqueous Br₂.