Question 1

Which of the following is not a step in the Suzuki reaction?

Accepted Answer

A)  Oxidative addition of R-X to the palladium catalyst
B)  Substitution of the R group to the palladium catalyst
C)  Transfer of the alkyl group from the organoborane to palladium
D)  Reductive elimination of R-R,forming the new C-C bondE) A) and B)
F) A) and C)

Question 2

What is the appropriate sequence of reagents that will produce the target molecule shown below from ethylbenzene? 2O2; (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) None of the above
F) A) and B)

Question 3

Identify the major organic product of the following reaction.

Accepted Answer

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

Question 4

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

Question 5

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) C) and D)

Question 6

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 gasE) C) and D)
F) A) and B)

Question 7

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

Accepted Answer

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

Question 8

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 B)
F) None of the above

Question 9

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

Question 10

What is the major organic product of the following reaction?

Accepted Answer

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

Question 11

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) 3E) A) and B)
F) All of the above

Question 12

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) A) and D)
F) A) and C)

Question 13

Identify the products of the following reaction.

Accepted Answer

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

Question 15

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) A) and B)
F) A) and C)

Question 16

What is the name for the type of intermediate X formed in the reaction sequence below?

Accepted Answer

A)  A carbocation
B)  A carbanion
C)  A free radical
D)  A carbeneE) B) and C)
F) A) and D)

Question 17

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.E) A) and B)
F) A) and C)

Question 18

Which of the following statements is not true about the Simmons-Smith reaction?

Accepted Answer

A)  The Simmons-Smith reaction involves the formation of a free carbene.
B)  The Simmons-Smith reaction uses the reagents zinc-copper couple.
C)  The Simmons-Smith reaction is stereospecific.
D)  The Simmons-Smith reaction involves CH2I2 reacting with a copper-activated zinc reagent.E) All of the above
F) C) and D)

Question 19

Identify the major organic product of the following reaction.

Accepted Answer

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

Question 20

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

Accepted Answer

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

Exam 24: Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

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

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What is the major organic product of the following reaction?

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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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Identify the products of the following reaction.

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

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

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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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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 of the following correctly describes a reaction yielding a dichorocarbene?

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What is the major organic product of the following reaction?

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What is the name for the type of intermediate X formed in the reaction sequence below?

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Which of the following is not a step in the Suzuki reaction?

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What products are formed when diazomethane is heated?

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

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Which of the following statements is not true about the Simmons-Smith 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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Identify the major organic product of the following reaction.

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

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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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