Question 1

Identify the starting material.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  The product cannot be formed directly from one of the reactants above. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  The product cannot be formed directly from one of the reactants above. D

Question 2

Which of the following statements is false regarding the preparation of organolithium compounds?

Accepted Answer

A)  Organolithium compounds can be made from alkyl halides (R-X). 
B)  Organolithium compounds can be made from aryl halides (Ar-X). 
C)  Vinyl halides cannot be used to form vinyl lithium reagents. 
D)  Lithium halides are byproducts of the reaction of lithium metal with alkyl halides. 
E)  It is necessary to use two equivalents of lithium metal. 
A)  Organolithium compounds can be made from alkyl halides (R-X). 
B)  Organolithium compounds can be made from aryl halides (Ar-X). 
C)  Vinyl halides cannot be used to form vinyl lithium reagents. 
D)  Lithium halides are byproducts of the reaction of lithium metal with alkyl halides. 
E)  It is necessary to use two equivalents of lithium metal. C

Question 3

Give the final product.

Accepted Answer

The answer of Give the final product.  ...

Question 4

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

Accepted Answer

A)  ethyl vinyl ketone and p-methylstyrene 
B)  ethyl vinyl ketone and 4-iodotoluene 
C)  p-methylstyrene and propionoyl chloride 
D)  (
E) -1-(2-bromovinyl)-4-methylbenzene and propionoyl chloride 
A)  ethyl vinyl ketone and p-methylstyrene 
B)  ethyl vinyl ketone and 4-iodotoluene 
C)  p-methylstyrene and propionoyl chloride 
D)  (
E) -1-(2-bromovinyl)-4-methylbenzene and propionoyl chloride

Question 5

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

Accepted Answer

A)  CH3CH2MgBr 
B)  CH3CH2MgI 
C)  (CH3CH2)2Zn 
D)  (CH3CH2)2Cu 
A)  CH3CH2MgBr 
B)  CH3CH2MgI 
C)  (CH3CH2)2Zn 
D)  (CH3CH2)2Cu

Question 6

Which of the following organozinc compounds can be used in a Negishi coupling reaction?

Accepted Answer

A)  a vinyl organozinc 
B)  an alkyl organozinc 
C)  an aryl organozinc 
D)  a benzyl organozinc 
E)  all of the above 
A)  a vinyl organozinc 
B)  an alkyl organozinc 
C)  an aryl organozinc 
D)  a benzyl organozinc 
E)  all of the above

Question 7

Which of the following statements is(are) true regarding the preparation of Gilman reagents?

Accepted Answer

A)  Gilman reagents can be made from alkyl halides (R-X). 
B)  Gilman reagents can be made from aryl halides (Ar-X). 
C)  Gilman reagents can be made from organolithium reagents. 
D)  Lithium halides are byproducts of the reaction to make Gilman reagents. 
E)  all of the above 
A)  Gilman reagents can be made from alkyl halides (R-X). 
B)  Gilman reagents can be made from aryl halides (Ar-X). 
C)  Gilman reagents can be made from organolithium reagents. 
D)  Lithium halides are byproducts of the reaction to make Gilman reagents. 
E)  all of the above

Question 8

Biselyngbyolide A is a cytotoxic natural product that shows promise for the treatment of bone lytic diseases. Shown below is a recent synthesis of this molecule (Org. Lett. 2014, 16, 2858). Give the structure of intermediate 1 and Biselyngbyolide
A. Hint: PPTS is a strong organic acid.

Accepted Answer

The first step is an intramole

Question 9

Which of the following is a boronic acid?

Accepted Answer

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

Question 10

Which of the following are possible Heck reaction products?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  all of the above 
A)  I 
B)  II 
C)  III 
D)  all of the above

Question 11

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

Accepted Answer

Cyclohexene and m-bromobenzald

Question 12

The Stille reaction couples organotin reagents with all but one of the following. Which is not a common coupling partner?

Accepted Answer

A)  -I 
B)  -Br 
C)  -Cl 
D)  -F 
E)  -OTf 
A)  -I 
B)  -Br 
C)  -Cl 
D)  -F 
E)  -OTf

Question 13

What is the product of the following reaction?

Accepted Answer

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

Question 14

Which of the following is not a mechanistic step in the generally accepted mechanism of the Stille coupling?

Accepted Answer

A)  transmetallation 
B)  reductive elimination 
C)  syn-elimination 
D)  oxidative addition 
A)  transmetallation 
B)  reductive elimination 
C)  syn-elimination 
D)  oxidative addition

Question 15

Identify the major product for the following reaction.

Accepted Answer

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

Question 16

What is the name of the product of the following reaction sequence?

Accepted Answer

4-methylbenzoic acid (Other ac

Question 17

What is the product of the following reaction?

Accepted Answer

A)  (2E,4Z)-4-methylhepta-2,4-diene 
B)  (2Z,4
E) -4-methylhepta-2,4-diene 
C)  (3E,5Z)-4-methylhepta-3,5-diene 
D)  (3Z,5Z)-4-methylhepta-3,5-diene 
E)  (3E,5
E) -4-methylhepta-3,5-diene 
A)  (2E,4Z)-4-methylhepta-2,4-diene 
B)  (2Z,4
E) -4-methylhepta-2,4-diene 
C)  (3E,5Z)-4-methylhepta-3,5-diene 
D)  (3Z,5Z)-4-methylhepta-3,5-diene 
E)  (3E,5
E) -4-methylhepta-3,5-diene

Question 18

A synthesis of the taxadienone system involves the following reaction (Org. Process. Res. Dev. 2015, 19, 284). What is the product?

Accepted Answer

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

Question 19

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 20

A report on the synthesis of Aromatic Erythrina Alkaloids uses the following transformation (Org. Lett. 2006, 8, 2143). Propose reasonable reaction conditions.

Accepted Answer

CHCl₃, t-BuOK (Actual

Exam 23: Introduction to Organometallic Compounds

Identify the starting material.

Which of the following statements is false regarding the preparation of organolithium compounds?

Give the final product.

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

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

Which of the following organozinc compounds can be used in a Negishi coupling reaction?

Which of the following statements is(are) true regarding the preparation of Gilman reagents?

Biselyngbyolide A is a cytotoxic natural product that shows promise for the treatment of bone lytic diseases. Shown below is a recent synthesis of this molecule (Org. Lett. 2014, 16, 2858). Give the structure of intermediate 1 and Biselyngbyolide A. Hint: PPTS is a strong organic acid.

Which of the following is a boronic acid?

Which of the following are possible Heck reaction products?

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

The Stille reaction couples organotin reagents with all but one of the following. Which is not a common coupling partner?

What is the product of the following reaction?

Which of the following is not a mechanistic step in the generally accepted mechanism of the Stille coupling?

Identify the major product for the following reaction.

What is the name of the product of the following reaction sequence?

What is the product of the following reaction?

A synthesis of the taxadienone system involves the following reaction (Org. Process. Res. Dev. 2015, 19, 284). What is the product?

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

A report on the synthesis of Aromatic Erythrina Alkaloids uses the following transformation (Org. Lett. 2006, 8, 2143). Propose reasonable reaction conditions.

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

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