Question 1

Which of the following statements is not true about the Simmons-Smith reaction?

Accepted Answer

A) The Simmons-Smith reaction involves the formation of a free carbene. 
B) The Simmons-Smith reaction uses the reagents zinc-copper couple. 
C) The Simmons-Smith reaction is stereospecific. 
D) The Simmons-Smith reaction involves CH2I2 reacting with a copper-activated zinc reagent. 
A) The Simmons-Smith reaction involves the formation of a free carbene. 
B) The Simmons-Smith reaction uses the reagents zinc-copper couple. 
C) The Simmons-Smith reaction is stereospecific. 
D) The Simmons-Smith reaction involves CH2I2 reacting with a copper-activated zinc reagent.

Question 2

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 3

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 4

Identify the products of the following reaction.

Accepted Answer

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

Question 5

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 6

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 7

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 8

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 9

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 10

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 11

Why is the Grubbs catalyst synthetically important?

Accepted Answer

A) Because it only requires dilute concentrations of the reactants 
B) Because it produces only stereospecific products 
C) Because it produces only stereoselective products 
D) Because it provides a synthetic pathway for ring-closing metathesis reactions 
A) Because it only requires dilute concentrations of the reactants 
B) Because it produces only stereospecific products 
C) Because it produces only stereoselective products 
D) Because it provides a synthetic pathway for ring-closing metathesis reactions

Question 12

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 13

What is the missing reactant in the following reaction?

Accepted Answer

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

Question 14

Identify the starting material that would be used to form the following product in a ring-closing metathesis reaction utilizing a Grubbs catalyst?

Accepted Answer

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

Question 15

Which of the following is not a step in the Suzuki reaction?

Accepted Answer

A) Oxidative addition of R-X to the palladium catalyst 
B) Substitution of the R group to the palladium catalyst 
C) Transfer of the alkyl group from the organoborane to palladium 
D) Reductive elimination of R-R, forming the new C-C bond 
A) Oxidative addition of R-X to the palladium catalyst 
B) Substitution of the R group to the palladium catalyst 
C) Transfer of the alkyl group from the organoborane to palladium 
D) Reductive elimination of R-R, forming the new C-C bond

Question 16

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 17

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

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

Which of the following statements is not true about the Simmons-Smith reaction?

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

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

Identify the products 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?

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

What products are formed when diazomethane is heated?

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

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

Why is the Grubbs catalyst synthetically important?

Identify the major organic product of the following reaction.

What is the missing reactant in the following reaction?

Identify the starting material that would be used to form the following product in a ring-closing metathesis reaction utilizing a Grubbs catalyst?

Which of the following is not a step in the Suzuki reaction?

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

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

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 Related Compounds

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

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

Synthetic Polymers

Lipids

Filters

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