Question 1

What are the conditions for the following reaction?

Accepted Answer

The answer of What are the conditions for the following...

Question 2

A total synthesis of ingenol utilized the Corey-Posner/Whitesides-House coupling reaction in a key C-C bond forming step (J. Am. Chem. Soc. 2002, 124, 9726). Propose a reagent to perform this transformation.

Accepted Answer

The answer of A total synthesis of ingenol utilized the...

Question 3

Which of the following electrophiles are commonly used with Gilman reagents to form C-C bonds?

Accepted Answer

A)  alkyl halides 
B)  aryl halides 
C)  vinyl halides 
D)  acyl halides 
E)  all the above 
A)  alkyl halides 
B)  aryl halides 
C)  vinyl halides 
D)  acyl halides 
E)  all the above

Question 4

Which is the major product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
A) I 
B) II 
C) III

Question 5

Identify the product when an ester reacts with two equivalents 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

What product results in the following reaction?

Accepted Answer

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

Question 7

Which of the following are products of the reaction below? Select all that apply.

Accepted Answer

A)   
B)   
C)   
D)   
A)   
B)   
C)   
D)

Question 8

Which of the following methods is not a common/useful way to make an organozinc reagent?

Accepted Answer

A)  alkyl halide + Zn in ether 
B)  alkyl halide + Mg followed by ZnBr2 
C)  organolithium +ZnBr2 
D)  organoborane + Zn 
A)  alkyl halide + Zn in ether 
B)  alkyl halide + Mg followed by ZnBr2 
C)  organolithium +ZnBr2 
D)  organoborane + Zn

Question 9

What functional group most typically results when a Grignard Reagent reacts with an acid halide, after aqueous workup?

Accepted Answer

The answer of What functional group most typically results when...

Question 10

Which of the following is false regarding ring-opening metathesis?

Accepted Answer

A)  Cyclic alkenes react to form dienes. 
B)  The Grubbs catalyst is commonly used. 
C)  Ethylene is typically formed in the reaction. 
D)  Ring opening metathesis can be performed in the presence of a variety of functional groups. 
A)  Cyclic alkenes react to form dienes. 
B)  The Grubbs catalyst is commonly used. 
C)  Ethylene is typically formed in the reaction. 
D)  Ring opening metathesis can be performed in the presence of a variety of functional groups.

Question 11

Starting from bromobenzene and ________ as the only source of carbon atoms, 1-phenylcyclohexene can be synthesized using a Corey-Posner/Whitesides-House coupling reaction.

Accepted Answer

A)  1-iodocyclohexene 
B)  3-iodocyclohexene 
C)  iodocyclohexane 
D)  (iodomethyl)cyclohexane 
A)  1-iodocyclohexene 
B)  3-iodocyclohexene 
C)  iodocyclohexane 
D)  (iodomethyl)cyclohexane

Question 12

Macrocyle A was formed by a two- step process involving a hydroboration of an alkene in B followed by an intramolecular Suzuki coupling of a vinyl iodide in B to form the indicated bond below. What is the structure of B? (Org. Lett. 2002, 4, 2205).

Accepted Answer

The answer of Macrocyle A was formed by a two-...

Question 13

Give the final product.

Accepted Answer

The answer of Give the final product.  ...

Question 14

What is the product of the following sequence?

Accepted Answer

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

Question 15

What is the major product for the following Heck Reaction?

Accepted Answer

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

Question 16

Which alkene would be used in the Heck reaction below?

Accepted Answer

A)   
B)   
C)   
D)   
A)   
B)   
C)   
D)

Question 17

Identify the product when formaldehyde 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 18

Which of the following alkenes is most reactive in the Heck reaction?

Accepted Answer

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

Question 19

What is the product of the following sequence?

Accepted Answer

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

Question 20

The reaction of a carbene with an alkene to make a cyclopropane commonly goes through which type mechanism?

Accepted Answer

A)  proton transfer 
B)  loss of leaving group 
C)  cycloaddition 
D)  α-elimination 
A)  proton transfer 
B)  loss of leaving group 
C)  cycloaddition 
D)  α-elimination

Exam 23: Introduction to Organometallic Compounds

What are the conditions for the following reaction?

A total synthesis of ingenol utilized the Corey-Posner/Whitesides-House coupling reaction in a key C-C bond forming step (J. Am. Chem. Soc. 2002, 124, 9726). Propose a reagent to perform this transformation.

Which of the following electrophiles are commonly used with Gilman reagents to form C-C bonds?

Which is the major product of the following reaction?

Identify the product when an ester reacts with two equivalents of a Grignard reagent.

What product results in the following reaction?

Which of the following are products of the reaction below? Select all that apply.

Which of the following methods is not a common/useful way to make an organozinc reagent?

What functional group most typically results when a Grignard Reagent reacts with an acid halide, after aqueous workup?

Which of the following is false regarding ring-opening metathesis?

Starting from bromobenzene and ________ as the only source of carbon atoms, 1-phenylcyclohexene can be synthesized using a Corey-Posner/Whitesides-House coupling reaction.

Macrocyle A was formed by a two- step process involving a hydroboration of an alkene in B followed by an intramolecular Suzuki coupling of a vinyl iodide in B to form the indicated bond below. What is the structure of B? (Org. Lett. 2002, 4, 2205).

Give the final product.

What is the product of the following sequence?

What is the major product for the following Heck Reaction?

Which alkene would be used in the Heck reaction below?

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

Which of the following alkenes is most reactive in the Heck reaction?

What is the product of the following sequence?

The reaction of a carbene with an alkene to make a cyclopropane commonly goes through which type mechanism?

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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