Question 1

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

Question 2

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

Accepted Answer

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

Question 3

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.

Question 4

Identify the major organic product of the following reaction.

Accepted Answer

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

Question 5

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.

Question 6

What is the major organic product of the following reaction?

Accepted Answer

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

Question 7

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.

Question 8

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.

Question 9

What is the major organic product of the following reaction?

Accepted Answer

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

Question 10

What is the major organic product of the following reaction?

Accepted Answer

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

Question 11

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? N1 mechanism. B)  The mechanism is a concerted. C)  The mechanism proceeds through a radical intermediate. D)  The mechanism is an E2 mechanism." class="answers-bank-image d-inline" rel="preload" >

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.

Question 12

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

Accepted Answer

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

Question 13

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.

Question 14

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

Question 15

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

Question 16

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

Accepted Answer

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

Question 17

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.

Question 18

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.

Question 19

Identify the major organic product of the following reaction.

Accepted Answer

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

Question 20

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.

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

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

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

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

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

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

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

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Which of the following descriptions does not apply to methylene?

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What is the major organic product of the following reaction?

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What is the major organic product of the following reaction?

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

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

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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?

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

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Identify the major organic product of the following reaction.

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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?

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What is the major organic product of the following reaction?

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

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

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Identify the major organic product of the following reaction.

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What products are formed when diazomethane is heated?

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

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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?

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