Question 1

What is the appropriate sequence of reagents that will produce the target molecule shown below from ethylbenzene?
 What is the appropriate sequence of reagents that will produce the target molecule shown below from ethylbenzene?   A) (1)  HBr, H2O2; (2)  KOC(CH3) 3 ; (3)  MCPBA; (4)  CH2=CPh2 B) (1)  NBS, hn ; (2)  KOC(CH3) 3 ; (3)  CHBr3, KO(CH3) 3 ; (4)  a.LiCuPh2, b.H2O C) (1)  H2SO4(aq.) , D ; (2)  MCPBA; (3)  CHBr3, KO(CH3) 3 ; (4)  CH2=CPh2 D) (1)  Br2, FeBr3 ; (2)  MCPBA; (3)  CHBr3, KO(CH3) 3 ; (4)  Ph2COCl" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  (1)  HBr, H2O2; (2)  KOC(CH3) 3 ; (3)  MCPBA; (4)  CH2=CPh2
B)  (1)  NBS, hn ; (2)  KOC(CH3) 3 ; (3)  CHBr3, KO(CH3) 3 ; (4)  a.LiCuPh2, b.H2O
C)  (1)  H2SO4(aq.) , D ; (2)  MCPBA; (3)  CHBr3, KO(CH3) 3 ; (4)  CH2=CPh2
D)  (1)  Br2, FeBr3 ; (2)  MCPBA; (3)  CHBr3, KO(CH3) 3 ; (4)  Ph2COClE) A) and C)
F) B) and C)

Question 2

Identify the major organic product of the following reaction.

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and D)
F) A) and C)

Question 3

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) All of the above
F) C) and D)

Question 4

Identify the major organic product of the following reaction.

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) C) and D)
F) None of the above

Question 5

What would be the major organic product of the following Heck reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) A) and B) C

Question 6

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.E) All of the above
F) B) and D)

Question 7

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 halidesE) A) and D)
F) All of the above

Question 8

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.E) C) and D)
F) A) and D) A

Question 9

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and D)
F) B) and C)

Question 10

Which of the following correctly describes a reaction yielding a dichorocarbene?

Accepted Answer

A)  The reaction of chloroform with KOC(CH3) 3.
B)  The reaction of chloroform with Zn(Cu) .
C)  The reaction of chloroform with (CH3) 2CuLi.
D)  The reaction of diazomethane with KOC(CH3) 3.E) A) and D)
F) None of the above

Question 11

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.E) None of the above
F) A) and D)

Question 12

Many of the reactions studied in this chapter are stereospecific.Why are stereospecific reactions important?

Accepted Answer

A)  When a reaction produces a mixture of enantiomers, it is often very difficult to separate them.A mixture of products is often not useful.
B)  Often stereoisomers of a particular compound will have very different biological effects on an organism.Only one isomer is biologically helpful, and the other may be harmful.
C)  Often only one stereoisomer is biologically active, and coupling reactions are often used for the production of biological materials.
D)  All of the choices are true.E) None of the above
F) B) and D)

Question 13

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?
 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?   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." 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.E) None of the above
F) All of the above

Question 14

What is the major organic product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) B) and C)

Question 15

What is the major organic product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  None of the choices is correct.E) A) and C)
F) B) and C)

Question 16

What is the appropriate sequence of starting material and reagents that will produce the target molecule shown below?
 What is the appropriate sequence of starting material and reagents that will produce the target molecule shown below?   A) I B) II C) III D) IV" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and D)
F) A) and C)

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)  IVE) A) and D)
F) B) and C)

Question 18

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.E) All of the above
F) B) and C) A

Question 19

Dichlorocarbene reacts with an alkene to form a cyclopropane derivative.In this reaction the dichlorocarbene acts as a(n)

Accepted Answer

A)  Lewis base.
B)  electrophile.
C)  nucleophile.
D)  Brønsted-Lowry base.E) A) and B)
F) B) and C)

Question 20

Which of the reactions listed below is not stereospecific?

Accepted Answer

A)  Suzuki reaction
B)  Organocuprate coupling reaction
C)  Heck reaction
D)  Simmons-Smith reactionE) A) and B)
F) A) and C)

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

What is the appropriate sequence of reagents that will produce the target molecule shown below from ethylbenzene?

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Identify the major organic product of the following reaction.

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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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What would be the major organic product of the following Heck reaction?

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Which of the following descriptions does not apply to methylene?

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

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Which of the following correctly describes a reaction yielding a dichorocarbene?

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

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Many of the reactions studied in this chapter are stereospecific.Why are stereospecific reactions important?

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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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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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What is the appropriate sequence of starting material and reagents that will produce the target molecule shown below?

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Identify the structure of the major organic product that results from 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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Dichlorocarbene reacts with an alkene to form a cyclopropane derivative.In this reaction the dichlorocarbene acts as a(n)

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Which of the reactions listed below is not stereospecific?

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C

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A

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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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A

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