Question 1

Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment with aqueous H2SO4)?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 2

What is the best choice of reagent(s) to perform the following transformation?

Accepted Answer

H₂, transit

Question 3

What type of carbocation is shown?

Accepted Answer

A)  primary 
B)  secondary 
C)  tertiary 
D)  quaternary 
A)  primary 
B)  secondary 
C)  tertiary 
D)  quaternary

Question 4

What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane?

Accepted Answer

A)  carbocation 
B)  carbanion 
C)  radical 
D)  cyclic bromonium ion 
A)  carbocation 
B)  carbanion 
C)  radical 
D)  cyclic bromonium ion

Question 5

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 6

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 7

The reduction of an alkene to an alkane by hydrogen in the presence of a catalyst is known as _____.

Accepted Answer

catalytic

Question 8

Provide the structure of the key intermediate in the following reaction?

Accepted Answer

The answer of Provide the structure of the key intermediate...

Question 9

What is the best choice of reagent(s) to perform the following transformation?

Accepted Answer

H₂O, H₂SO₄ or

Question 10

What is the best choice of reagent(s) to perform the following transformation?

Accepted Answer

A)  H2O, H2SO4 
B)  HgSO4; followed by NaBH4 
C)  BH3; followed by H2O2 
D)  OsO4; followed by NaHSO3 
A)  H2O, H2SO4 
B)  HgSO4; followed by NaBH4 
C)  BH3; followed by H2O2 
D)  OsO4; followed by NaHSO3

Question 11

Which of the following concepts explains Markovnikov's rule as applied to the addition of HBr to propene?

Accepted Answer

A)  the relative stability of carbocations 
B)  the nucleophilicity of bromide anion 
C)  the acidity of HBr 
D)  the aufbau principle 
A)  the relative stability of carbocations 
B)  the nucleophilicity of bromide anion 
C)  the acidity of HBr 
D)  the aufbau principle

Question 12

"X" is a naturally occurring terpenoid with the molecular formula C10H18O. It is isolated from geranium oil. "X" reacts with (S)-BINAP-RuCl3 and (R)-BINAP-RuCl3 to form A and B, respectively. Identify "X". ​

Accepted Answer

A)  Naproxen 
B)  Geraniol 
C)  Cannabinoid 
D)  Curcuminoid 
A)  Naproxen 
B)  Geraniol 
C)  Cannabinoid 
D)  Curcuminoid

Question 13

What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an alcohol?

Accepted Answer

A)  nucleophilic addition 
B)  electrophilic addition 
C)  radical addition 
D)  elimination 
A)  nucleophilic addition 
B)  electrophilic addition 
C)  radical addition 
D)  elimination

Question 14

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 15

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

Accepted Answer

The reaction proceeds in two s

Question 16

Identify "X" and "Y" in the following reaction. ​

Accepted Answer

A)  X is 1-methylcyclopentene, and Y is Br2/H2O in DMSO. 
B)  X is cyclopentene, and Y is Pd/H2. 
C)  X is cyclopentadiene, and Y is H2O. 
D)  X is 2-methylcyclopentadiene, and Y is Br2 in DMSO. 
A)  X is 1-methylcyclopentene, and Y is Br2/H2O in DMSO. 
B)  X is cyclopentene, and Y is Pd/H2. 
C)  X is cyclopentadiene, and Y is H2O. 
D)  X is 2-methylcyclopentadiene, and Y is Br2 in DMSO.

Question 17

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 18

What is (are) the major organic product(s) obtained from the following reaction?

Accepted Answer

A)  only 1 
B)  only 2 
C)  only 3 
D)  only 2 and 3 
A)  only 1 
B)  only 2 
C)  only 3 
D)  only 2 and 3

Question 19

Br2 in CCl4 can be used to distinguish cyclohexene from cyclohexane.

Accepted Answer

A) True 
 B)False

Question 20

Consider the following reaction sequence.   The product of this sequence is

Accepted Answer

A) True 
 B)False

Exam 6: Reactions of Alkenes

Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment with aqueous H2SO4)?

What is the best choice of reagent(s) to perform the following transformation?

What type of carbocation is shown?

What type of reactive intermediate is formed in the reaction of an alkene with HBr to give a bromoalkane?

What is the major organic product obtained from the following reaction?

What is the major organic product obtained from the following reaction?

The reduction of an alkene to an alkane by hydrogen in the presence of a catalyst is known as _____.

Provide the structure of the key intermediate in the following reaction?

What is the best choice of reagent(s) to perform the following transformation?

What is the best choice of reagent(s) to perform the following transformation?

Which of the following concepts explains Markovnikov's rule as applied to the addition of HBr to propene?

"X" is a naturally occurring terpenoid with the molecular formula C10H18O. It is isolated from geranium oil. "X" reacts with (S)-BINAP-RuCl3 and (R)-BINAP-RuCl3 to form A and B, respectively. Identify "X". ​

What type of reaction mechanism accounts for the reaction of an alkene with aqueous acid to give an alcohol?

What is the major organic product obtained from the following reaction?

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

Identify "X" and "Y" in the following reaction. ​

What is the major organic product obtained from the following reaction?

What is (are) the major organic product(s) obtained from the following reaction?

Br2 in CCl4 can be used to distinguish cyclohexene from cyclohexane.

Consider the following reaction sequence. The product of this sequence is

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment with aqueous H₂SO₄)?

"X" is a naturally occurring terpenoid with the molecular formula C₁₀H₁₈O. It is isolated from geranium oil. "X" reacts with (S)-BINAP-RuCl₃ and (R)-BINAP-RuCl₃ to form A and B, respectively. Identify "X".

Identify "X" and "Y" in the following reaction.

Br₂in CCl₄ can be used to distinguish cyclohexene from cyclohexane.