Question 1

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

Accepted Answer

A)  dihydroxylation using OsO4, H2O2 
B)  addition of H2 
C)  hydroboration, oxidation 
D)  addition of HCl 
E)  A, B, and C 
A)  dihydroxylation using OsO4, H2O2 
B)  addition of H2 
C)  hydroboration, oxidation 
D)  addition of HCl 
E)  A, B, and C

Question 2

What is (are) the expected major product(s) for the following reaction sequence?

Accepted Answer

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

Question 3

Provide the organic product(s) for the reaction 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 4

The reaction of Br2 with 1-methylcyclohexene, in the presence of ethylamine (EtNH2), is expected to produce which of the following as the major product?

Accepted Answer

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

Question 5

The decrease in entropy (the $\Delta$S value is negative) observed for alkene addition reactions results from _______.

Accepted Answer

A)  the breaking of a π and $\sigma$ bond. 
B)  the formation of two $\sigma$ bonds. 
C)  the reaction being exothermic. 
D)  two molecules reacting to form a single molecule. 
E)  the temperature dependence of the $\Delta$S term. 
A)  the breaking of a π and $\sigma$ bond. 
B)  the formation of two $\sigma$ bonds. 
C)  the reaction being exothermic. 
D)  two molecules reacting to form a single molecule. 
E)  the temperature dependence of the $\Delta$S term.

Question 6

The alkene precursor to acetone is __________.

Accepted Answer

propylene

Question 7

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 8

What major product is expected from 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 9

For the reaction sequence below, identify the expected major product(s).

Accepted Answer

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

Question 10

What is the name of the product formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H2?

Accepted Answer

A)  1-chloro-2-methylcyclohexane 
B)  1-chloro-3-methylcyclohexane 
C)  1-chloro-5-methylcyclohexane 
D)  3-chloro-1-methylcyclohexane 
E)  None of the above 
A)  1-chloro-2-methylcyclohexane 
B)  1-chloro-3-methylcyclohexane 
C)  1-chloro-5-methylcyclohexane 
D)  3-chloro-1-methylcyclohexane 
E)  None of the above

Question 11

Identify the structure(s) of the expected major organic product(s) of the following reaction. Draw the products in the expected chair conformations and include regiochemical and/or stereochemical details as needed.

Accepted Answer

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

Question 12

A common problem in the acid-catalyzed hydration of alkenes is the formation of an ether byproduct. Explain the formation of the ether byproduct in relation to the reaction below:

Accepted Answer

The answer of A common problem in the acid-catalyzed hydration...

Question 13

Which of the following sets of reagents accomplishes the synthesis shown below?

Accepted Answer

A)  H2/HCl 
B)  H2/H2SO4 
C)  H2/Ni 
D)  H2O/Ni 
E)  H2O/H2SO4 
A)  H2/HCl 
B)  H2/H2SO4 
C)  H2/Ni 
D)  H2O/Ni 
E)  H2O/H2SO4

Question 14

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and catalytic OsO4 with NMO.

Accepted Answer

SHAPE \* MERGEFORMAT @#IMG-DLM&_TB4454_0

Question 15

The synthesis shown below generates an achiral product from a chiral starting material. Provide the structure of the expected product and a mechanism explaining the synthesis. Briefly explain why the product formed is achiral.

Accepted Answer

@#IMG-DLM&_TB4454_00 @#IMG-DLM&_TB4454_00 Upon addition of t

Question 16

For the following equation, provide a detailed step-wise mechanism showing the electron flow using the curved arrow formalism.
SHAPE \* MERGEFORMAT

Accepted Answer

The answer of For the following equation, provide a detailed...

Question 17

What is the expected major product(s) of HCl addition to the alkene below?

Accepted Answer

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

Question 18

Give the best description of the regioselectivity and stereospecificity in the oxymercuration of an alkene.

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 19

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 20

A reaction that could potentially yield two or more constitutional isomers, but as in hydroboration-oxidation produces only one isomer, is said to be _____________________.

Accepted Answer

The answer of A reaction that could potentially yield two...

Exam 8: Addition Reactions of Alkenes

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

What is (are) the expected major product(s) for the following reaction sequence?

Provide the organic product(s) for the reaction shown below.

The reaction of Br2 with 1-methylcyclohexene, in the presence of ethylamine (EtNH2), is expected to produce which of the following as the major product?

The decrease in entropy (the Δ\DeltaΔ S value is negative) observed for alkene addition reactions results from _______.

The alkene precursor to acetone is __________.

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

What major product is expected from the following reaction?

For the reaction sequence below, identify the expected major product(s).

What is the name of the product formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H2?

Identify the structure(s) of the expected major organic product(s) of the following reaction. Draw the products in the expected chair conformations and include regiochemical and/or stereochemical details as needed.

A common problem in the acid-catalyzed hydration of alkenes is the formation of an ether byproduct. Explain the formation of the ether byproduct in relation to the reaction below:

Which of the following sets of reagents accomplishes the synthesis shown below?

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and catalytic OsO4 with NMO.

The synthesis shown below generates an achiral product from a chiral starting material. Provide the structure of the expected product and a mechanism explaining the synthesis. Briefly explain why the product formed is achiral.

For the following equation, provide a detailed step-wise mechanism showing the electron flow using the curved arrow formalism. SHAPE \* MERGEFORMAT

What is the expected major product(s) of HCl addition to the alkene below?

Give the best description of the regioselectivity and stereospecificity in the oxymercuration of an alkene.

What is the expected major product for the following reaction?

A reaction that could potentially yield two or more constitutional isomers, but as in hydroboration-oxidation produces only one isomer, is said to be _____________________.

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

The reaction of Br₂ with 1-methylcyclohexene, in the presence of ethylamine (EtNH₂), is expected to produce which of the following as the major product?

The decrease in entropy (the $\Delta$ S value is negative) observed for alkene addition reactions results from _______.

What is the name of the product formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H₂?

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and catalytic OsO₄ with NMO.