Question 1

Identify the structure of the major organic product that results from the following reaction.

Accepted Answer

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

Question 2

Which class of compounds listed below does not react with organocuprate reagents to form a coupling product that contains a new carbon-carbon bond?

Accepted Answer

A)  1° alkyl halides 
B)  3° alkyl halides 
C)  vinyl halides 
D)  aryl halides 
A)  1° alkyl halides 
B)  3° alkyl halides 
C)  vinyl halides 
D)  aryl halides

Question 3

Identify the major organic product of the following reaction.

Accepted Answer

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

Question 4

As shown below, when cis-2-butene reacts with dichlorocarbene, only the cis-1,1-dichloro-2,3-dimethylcyclopropane is formed. What can we conclude about the nature of the reaction mechanism?

Accepted Answer

A)  The mechanism is an SN1 mechanism. 
B)  The mechanism is a concerted. 
C)  The mechanism proceeds through a radical intermediate. 
D)  The mechanism is an E2 mechanism. 
A)  The mechanism is an SN1 mechanism. 
B)  The mechanism is a concerted. 
C)  The mechanism proceeds through a radical intermediate. 
D)  The mechanism is an E2 mechanism.

Question 5

Organocuprate reagents (R2CuLi) react with several compounds. Which listed reaction is not correct?

Accepted Answer

A)  Acid chlorides react with organocuprate reagents to form ketones. 
B)  Epoxides react with organocuprate reagents to form alcohols. 
C)  Alkyl halides react with organocuprate reagents to form coupling products containing a new carbon-carbon bond. 
D)  Carbon dioxide reacts with organocuprate reagents to form carboxylic acids. 
A)  Acid chlorides react with organocuprate reagents to form ketones. 
B)  Epoxides react with organocuprate reagents to form alcohols. 
C)  Alkyl halides react with organocuprate reagents to form coupling products containing a new carbon-carbon bond. 
D)  Carbon dioxide reacts with organocuprate reagents to form carboxylic acids.

Question 6

Which of the following statements is not true about a carbene?

Accepted Answer

A)  A carbene is a neutral reactive intermediate. 
B)  A carbene contains a divalent carbon. 
C)  A carbene is sp3 hybridized. 
D)  A carbene is surrounded by six electrons. 
A)  A carbene is a neutral reactive intermediate. 
B)  A carbene contains a divalent carbon. 
C)  A carbene is sp3 hybridized. 
D)  A carbene is surrounded by six electrons.

Question 7

Which statement below best explains what is meant by the statement, "An organocuprate reaction with a vinyl halide is stereospecific"?

Accepted Answer

A)  The reaction of a specific stereoisomer with the R2CuLi reagent will yield that particular stereoisomer as the product. 
B)  The reaction of a vinyl halide with the R2CuLi reagent will only yield the cis product. 
C)  The reaction of a vinyl halide with the R2CuLi reagent will only yield the trans product. 
D)  The reaction of a vinyl halide with the R2CuLi reagent will only yield one enantiomer product-either R or S configuration. 
A)  The reaction of a specific stereoisomer with the R2CuLi reagent will yield that particular stereoisomer as the product. 
B)  The reaction of a vinyl halide with the R2CuLi reagent will only yield the cis product. 
C)  The reaction of a vinyl halide with the R2CuLi reagent will only yield the trans product. 
D)  The reaction of a vinyl halide with the R2CuLi reagent will only yield one enantiomer product-either R or S configuration.

Question 8

Choose the statement below that is not true about the Suzuki reaction.

Accepted Answer

A)  The product of the Suzuki reaction is completely stereospecific. 
B)  The Suzuki reaction involves both an organoborane reagent and an organopalladium catalyst. 
C)  The Suzuki reaction forms more highly substituted alkenes. 
D)  The Suzuki reaction involves an oxidative addition followed by a reductive elimination. 
A)  The product of the Suzuki reaction is completely stereospecific. 
B)  The Suzuki reaction involves both an organoborane reagent and an organopalladium catalyst. 
C)  The Suzuki reaction forms more highly substituted alkenes. 
D)  The Suzuki reaction involves an oxidative addition followed by a reductive elimination.

Question 9

What is the major organic product of the following reaction?

Accepted Answer

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

Question 10

What products are formed when diazomethane is heated?

Accepted Answer

A)  methane gas and nitrogen gas 
B)  propene gas and nitrogen gas 
C)  methyl radical and nitrogen gas 
D)  methylene and nitrogen gas 
A)  methane gas and nitrogen gas 
B)  propene gas and nitrogen gas 
C)  methyl radical and nitrogen gas 
D)  methylene and nitrogen gas

Question 11

What would be the starting material for the following product that was made via a Grubbs catalyst?

Accepted Answer

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

Question 12

What is the major organic product of the following reaction?

Accepted Answer

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

Question 13

Which of the following is true about the use of the Grubbs catalyst?

Accepted Answer

A)  The Grubbs catalyst is used in carbon-carbon coupling reactions. 
B)  The Grubbs catalyst is used in alkene metathesis. 
C)  The Grubbs catalyst is used in carbene formation. 
D)  The Grubbs catalyst is used with palladium as a co-catalyst. 
A)  The Grubbs catalyst is used in carbon-carbon coupling reactions. 
B)  The Grubbs catalyst is used in alkene metathesis. 
C)  The Grubbs catalyst is used in carbene formation. 
D)  The Grubbs catalyst is used with palladium as a co-catalyst.

Question 14

What is the major organic product of the following reaction?

Accepted Answer

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

Question 15

What do the Suzuki reaction, the Heck reaction, and the organocuprate reaction all have in common when they react with an alkyl halide?

Accepted Answer

A)  All reactions form new carbon-carbon bonds. 
B)  They all use palladium as a catalyst in one step of the reaction. 
C)  They are all stereospecific reactions. 
D)  They all require harsh conditions. 
A)  All reactions form new carbon-carbon bonds. 
B)  They all use palladium as a catalyst in one step of the reaction. 
C)  They are all stereospecific reactions. 
D)  They all require harsh conditions.

Question 16

Identify the structure of the organic product Y formed in the following reaction sequence.

Accepted Answer

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

Question 17

What starting material could yield the following compound if Simmons-Smith conditions were used?

Accepted Answer

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

Question 18

Identify the major organic product of the following reaction.

Accepted Answer

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

Question 19

Which of the following descriptions does not apply to methylene?

Accepted Answer

A)  Methylene is sp2 hybridized. 
B)  Methylene is a neutral, reactive intermediate. 
C)  Methylene is a radical intermediate. 
D)  The formula of methylene is :CH2. 
A)  Methylene is sp2 hybridized. 
B)  Methylene is a neutral, reactive intermediate. 
C)  Methylene is a radical intermediate. 
D)  The formula of methylene is :CH2.

Question 20

Coupling reactions with vinyl halides are stereospecific. Which choice below best describes the expected product when trans-1-bromo-1-hexene reacts with (CH3)2CuLi?

Accepted Answer

A)  The reaction will only yield a trans-alkene. 
B)  The reaction will only yield a cis-alkene. 
C)  The reaction will only yield one enantiomeric product with R configuration. 
D)  The reaction will only yield one enantiomeric product with S configuration. 
A)  The reaction will only yield a trans-alkene. 
B)  The reaction will only yield a cis-alkene. 
C)  The reaction will only yield one enantiomeric product with R configuration. 
D)  The reaction will only yield one enantiomeric product with S configuration.

Exam 26: Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Identify the structure of the major organic product that results from the following reaction.

Which class of compounds listed below does not react with organocuprate reagents to form a coupling product that contains a new carbon-carbon bond?

Identify the major organic product of the following reaction.

As shown below, when cis-2-butene reacts with dichlorocarbene, only the cis-1,1-dichloro-2,3-dimethylcyclopropane is formed. What can we conclude about the nature of the reaction mechanism?

Organocuprate reagents (R2CuLi) react with several compounds. Which listed reaction is not correct?

Which of the following statements is not true about a carbene?

Which statement below best explains what is meant by the statement, "An organocuprate reaction with a vinyl halide is stereospecific"?

Choose the statement below that is not true about the Suzuki reaction.

What is the major organic product of the following reaction?

What products are formed when diazomethane is heated?

What would be the starting material for the following product that was made via a Grubbs catalyst?

What is the major organic product of the following reaction?

Which of the following is true about the use of the Grubbs catalyst?

What is the major organic product of the following reaction?

What do the Suzuki reaction, the Heck reaction, and the organocuprate reaction all have in common when they react with an alkyl halide?

Identify the structure of the organic product Y formed in the following reaction sequence.

What starting material could yield the following compound if Simmons-Smith conditions were used?

Identify the major organic product of the following reaction.

Which of the following descriptions does not apply to methylene?

Coupling reactions with vinyl halides are stereospecific. Which choice below best describes the expected product when trans-1-bromo-1-hexene reacts with (CH3)2CuLi?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

Organocuprate reagents (R₂CuLi) react with several compounds. Which listed reaction is not correct?

Coupling reactions with vinyl halides are stereospecific. Which choice below best describes the expected product when trans-1-bromo-1-hexene reacts with (CH₃)₂CuLi?