Question 1

What is the expected major product for the following reaction?

Accepted Answer

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

Question 2

Which of the following will yield 2-methylpentane upon catalytic hydrogenation?

Accepted Answer

A)  2-methyl-1-pentene2 
B)  2-methyl-2-pentene 
C)  4-methyl-2-pentene 
D)  4-methyl-1-pentene 
E)  All of the above 
A)  2-methyl-1-pentene2 
B)  2-methyl-2-pentene 
C)  4-methyl-2-pentene 
D)  4-methyl-1-pentene 
E)  All of the above

Question 3

The expected product(s) resulting from addition of Br2 to (E)-3-hexene would be:

Accepted Answer

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

Question 4

What is the IUPAC name of the expected major product formed upon reaction of HCl with 3-methyl-1-butene?

Accepted Answer

A)  1-chloro-2-methylbutane 
B)  1-chloro-3-methylbutane 
C)  2-chloro-2-methylbutane 
D)  2-chloro-3-methylbutane 
E)  1-chloropentane 
A)  1-chloro-2-methylbutane 
B)  1-chloro-3-methylbutane 
C)  2-chloro-2-methylbutane 
D)  2-chloro-3-methylbutane 
E)  1-chloropentane

Question 5

The regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene is best described as:

Accepted Answer

A)  Markovnikov orientation with syn-addition 
B)  Markovnikov orientation with anti-addition 
C)  Anti-Markovnikov orientation with syn-addition 
D)  Anti-Markovnikov orientation with anti-addition 
E)  Markovnikov orientation with both syn- and anti-addition 
A)  Markovnikov orientation with syn-addition 
B)  Markovnikov orientation with anti-addition 
C)  Anti-Markovnikov orientation with syn-addition 
D)  Anti-Markovnikov orientation with anti-addition 
E)  Markovnikov orientation with both syn- and anti-addition

Question 6

Identify the expected major organic product resulting from 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 7

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 B and D 
A)    
B)    
C)    
D)    
E)  Both B and D

Question 8

In conducting a catalytic hydrogenation of an alkene, which catalyst listed is most likely soluble in the reaction medium?

Accepted Answer

A)  Ni 
B)  Pt 
C)  Pd 
D)  Wilkinson's catalyst 
E)  All of the above are soluble 
A)  Ni 
B)  Pt 
C)  Pd 
D)  Wilkinson's catalyst 
E)  All of the above are soluble

Question 9

Consider the information given below and identify the structure of the unknown compound A, with a molecular formula of C8H14. Compound A reacts with Br2/CCl4. Upon reaction of A with excess H2/Ni 1-ethyl-2-methylcyclopentane is produced. Subjecting A to ozonolysis, the product shown below is produced as the major organic product. Draw the correct structure of compound A, and provide a brief and clear explanation relating the data provide with the structure selected.

Accepted Answer

A must be 3-ethyl-4-

Question 10

What is the expected major product upon reaction of 1-pentene with Cl2?

Accepted Answer

A)  1-chloropentane 
B)  2-chloropentane 
C)  1,1-dichloropentane 
D)  2,2-dichloropentane 
E)  1,2-dichloropentane 
A)  1-chloropentane 
B)  2-chloropentane 
C)  1,1-dichloropentane 
D)  2,2-dichloropentane 
E)  1,2-dichloropentane

Question 11

Provide the expected major organic product from the reaction shown below. Provide a brief explanation of any regioselectivity the reaction is expected to produce.

Accepted Answer

@#IMG-DLM& The alcohol will be found at the tertia

Question 12

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 13

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 14

The regioselectivity and stereospecificity in the oxymercuration of an alkene is best described as:

Accepted Answer

A)  Markovnikov orientation with syn-addition 
B)  Markovnikov orientation with anti-addition 
C)  anti-Markovnikov orientation with syn-addition 
D)  anti-Markovnikov orientation with anti-addition 
E)  Markovnikov orientation with both syn- and anti-addition 
A)  Markovnikov orientation with syn-addition 
B)  Markovnikov orientation with anti-addition 
C)  anti-Markovnikov orientation with syn-addition 
D)  anti-Markovnikov orientation with anti-addition 
E)  Markovnikov orientation with both syn- and anti-addition

Question 15

For the following transformation below, provide a detailed step-wise mechanism showing the electron flow using the curved arrow formalism.

Accepted Answer

The answer of For the following transformation below, provide a...

Question 16

What is the expected major product for the following reaction?

Accepted Answer

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

Question 17

Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?

Accepted Answer

A)  2,3-dibromo-2-methylpentane 
B)  2,2-dibromo-3-methylpentane 
C)  3,3-dibromo-2-methylpentane 
D)  2-bromo-2-methylpentane 
E)  3-bromo-2-methylpentane 
A)  2,3-dibromo-2-methylpentane 
B)  2,2-dibromo-3-methylpentane 
C)  3,3-dibromo-2-methylpentane 
D)  2-bromo-2-methylpentane 
E)  3-bromo-2-methylpentane

Question 18

For the following reaction draw out the expected major organic product(s). Include regiochemical and/or stereochemical details as relevant, and provide a short justification for the product(s) drawn.

Accepted Answer

@#IMG-DLM& The reaction takes place with

Question 19

What is the expected major product of 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 20

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

Accepted Answer

A)  Markovnikov addition of H2O, promoting skeletal rearrangement 
B)  Markovnikov addition of H2O, preventing skeletal rearrangement 
C)  anti-Markovnikov addition of H2O, promoting skeletal rearrangement 
D)  anti-Markovnikov addition of H2O, preventing skeletal rearrangement 
E)  anti-Markovnikov addition of H2O, syn-hydroxylation 
A)  Markovnikov addition of H2O, promoting skeletal rearrangement 
B)  Markovnikov addition of H2O, preventing skeletal rearrangement 
C)  anti-Markovnikov addition of H2O, promoting skeletal rearrangement 
D)  anti-Markovnikov addition of H2O, preventing skeletal rearrangement 
E)  anti-Markovnikov addition of H2O, syn-hydroxylation

Exam 9: Addition Reactions of Alkenes

What is the expected major product for the following reaction?

Which of the following will yield 2-methylpentane upon catalytic hydrogenation?

The expected product(s) resulting from addition of Br2 to (E)-3-hexene would be:

What is the IUPAC name of the expected major product formed upon reaction of HCl with 3-methyl-1-butene?

The regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene is best described as:

Identify the expected major organic product resulting from the following reaction sequence.

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

In conducting a catalytic hydrogenation of an alkene, which catalyst listed is most likely soluble in the reaction medium?

What is the expected major product upon reaction of 1-pentene with Cl2?

Provide the expected major organic product from the reaction shown below. Provide a brief explanation of any regioselectivity the reaction is expected to produce.

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

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

The regioselectivity and stereospecificity in the oxymercuration of an alkene is best described as:

For the following transformation below, provide a detailed step-wise mechanism showing the electron flow using the curved arrow formalism.

What is the expected major product for the following reaction?

Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?

For the following reaction draw out the expected major organic product(s). Include regiochemical and/or stereochemical details as relevant, and provide a short justification for the product(s) drawn.

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

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

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

The expected product(s) resulting from addition of Br₂ to (E)-3-hexene would be:

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

What is the expected major product upon reaction of 1-pentene with Cl₂?

Treating 2-methyl-2-pentene with Br₂ is expected to produce which of the following as the major product?