Question 1

Which of the following statements is false regarding the reactivity of Gilman reagents?

Accepted Answer

A)  They react with acyl halides to give ketones. 
B)  They react with α,β-unsaturated ketones to give alcohols. 
C)  They react with alkyl halides or aryl halides in a coupling reaction. 
D)  They are unreactive with tertiary halides. 
A)  They react with acyl halides to give ketones. 
B)  They react with α,β-unsaturated ketones to give alcohols. 
C)  They react with alkyl halides or aryl halides in a coupling reaction. 
D)  They are unreactive with tertiary halides.

Question 2

Draw the product(s) of the following reaction:

Accepted Answer

The answer of Draw the product(s) of the following reaction:...

Question 3

The Heck reaction requires the presence of a base.

Accepted Answer

A) True 
 B)False

Question 4

Which of the following R groups (R-SnBu3) would undergo the fastest transmetallation in a Stille coupling reaction?

Accepted Answer

A)  alkyl 
B)  aryl 
C)  vinyl 
D)  benzyl 
A)  alkyl 
B)  aryl 
C)  vinyl 
D)  benzyl

Question 5

Identify the product when butanal reacts with one equivalent of a Grignard reagent.

Accepted Answer

A)  primary alcohol 
B)  secondary alcohol 
C)  tertiary alcohol 
D)  carboxylic acid 
E)  ketone 
A)  primary alcohol 
B)  secondary alcohol 
C)  tertiary alcohol 
D)  carboxylic acid 
E)  ketone

Question 6

Which catalysts are common in the Stille coupling reaction?

Accepted Answer

A)  Pd(PPh3)4 
B)  Pd (OAc)2 
C)  PdCl2(PPh3)2 
D)  All of the above 
A)  Pd(PPh3)4 
B)  Pd (OAc)2 
C)  PdCl2(PPh3)2 
D)  All of the above

Question 7

Which of the following would react fastest in the Corey-Posner/Whitesides-House reaction?

Accepted Answer

A)  cyclohexyl chloride 
B)  cyclohexyl iodide 
C)  tert-butyl chloride 
D)  tert-butyl iodide 
A)  cyclohexyl chloride 
B)  cyclohexyl iodide 
C)  tert-butyl chloride 
D)  tert-butyl iodide

Question 8

Which of the following Gilman reagents could be used with a vinyl halide to afford the (E,E)-diene shown below? Select all that apply.

Accepted Answer

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

Question 9

Which of the following compounds has the most ionic character in the C-M bond?

Accepted Answer

A)  HC≡CMgBr 
B)  HC≡CK 
C)  HC≡CNa 
D)  HC≡CLi 
A)  HC≡CMgBr 
B)  HC≡CK 
C)  HC≡CNa 
D)  HC≡CLi

Question 10

Which of the following compounds has the most nucleophilic carbon atom?

Accepted Answer

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

Question 11

What is the product of the following ring-closing metathesis reaction?

Accepted Answer

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

Question 12

What is the product of the following sequence?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) none of the them 
A) I 
B) II 
C) III 
D) IV 
E) none of the them

Question 13

What product(s) result in the following reaction? Select all that apply.

Accepted Answer

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

Question 14

What is the product of the following reaction?

Accepted Answer

The answer of What is the product of the following...

Question 15

What is the product of the following sequence?

Accepted Answer

The answer of What is the product of the following...

Question 16

Which of the following R groups (R-SnBu3) would undergo the slowest transmetallation in a Stille coupling reaction?

Accepted Answer

A)  alkyl 
B)  aryl 
C)  vinyl 
D)  benzyl 
A)  alkyl 
B)  aryl 
C)  vinyl 
D)  benzyl

Question 17

Identify the coupling partners that can be used to prepare the following compound in a Heck reaction.

Accepted Answer

A)  p-nitrostyrene and (
E) -(2-bromovinyl)benzene 
B)  p-nitrostyrene and (Z)-(2-bromovinyl)benzene 
C)  (
E) -1-(2-bromovinyl)-4-nitrobenzene and styrene 
D)  (Z)-1-(2-bromovinyl)-4-nitrobenzene and styrene 
A)  p-nitrostyrene and (
E) -(2-bromovinyl)benzene 
B)  p-nitrostyrene and (Z)-(2-bromovinyl)benzene 
C)  (
E) -1-(2-bromovinyl)-4-nitrobenzene and styrene 
D)  (Z)-1-(2-bromovinyl)-4-nitrobenzene and styrene

Question 18

Explain why the solvent for a Grignard reaction must be free of water.

Accepted Answer

Water cons

Question 19

Which of the following are advantages of the Suzuki coupling over the Stille coupling? Select all that apply.

Accepted Answer

A) Organoboron compounds are less expensive than organotin compounds. 
B) Organoboron compounds are less toxic than organotin compounds. 
C) Formation of alkyl-aryl bonds is possible. 
D) The reaction requires a base. 
A) Organoboron compounds are less expensive than organotin compounds. 
B) Organoboron compounds are less toxic than organotin compounds. 
C) Formation of alkyl-aryl bonds is possible. 
D) The reaction requires a base.

Question 20

What is the product of the following reaction?

Accepted Answer

A)  (
E) -1-phenyl-1-pentene 
B)  (Z)-1-phenyl-1-pentene 
C)  (
E) -1-phenyl-2-pentene 
D)  (Z)-1-phenyl-2-pentene 
E)  2-phenyl-1-pentene 
A)  (
E) -1-phenyl-1-pentene 
B)  (Z)-1-phenyl-1-pentene 
C)  (
E) -1-phenyl-2-pentene 
D)  (Z)-1-phenyl-2-pentene 
E)  2-phenyl-1-pentene

Exam 23: Introduction to Organometallic Compounds

Which of the following statements is false regarding the reactivity of Gilman reagents?

Draw the product(s) of the following reaction:

The Heck reaction requires the presence of a base.

Which of the following R groups (R-SnBu3) would undergo the fastest transmetallation in a Stille coupling reaction?

Identify the product when butanal reacts with one equivalent of a Grignard reagent.

Which catalysts are common in the Stille coupling reaction?

Which of the following would react fastest in the Corey-Posner/Whitesides-House reaction?

Which of the following Gilman reagents could be used with a vinyl halide to afford the (E,E)-diene shown below? Select all that apply.

Which of the following compounds has the most ionic character in the C-M bond?

Which of the following compounds has the most nucleophilic carbon atom?

What is the product of the following ring-closing metathesis reaction?

What is the product of the following sequence?

What product(s) result in the following reaction? Select all that apply.

What is the product of the following reaction?

What is the product of the following sequence?

Which of the following R groups (R-SnBu3) would undergo the slowest transmetallation in a Stille coupling reaction?

Identify the coupling partners that can be used to prepare the following compound in a Heck reaction.

Explain why the solvent for a Grignard reaction must be free of water.

Which of the following are advantages of the Suzuki coupling over the Stille coupling? Select all that apply.

What is the product of the following reaction?

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

Addition Reactions of Alkenes

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

Which of the following R groups (R-SnBu₃) would undergo the fastest transmetallation in a Stille coupling reaction?

Which of the following R groups (R-SnBu₃) would undergo the slowest transmetallation in a Stille coupling reaction?