Question 1

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. 
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. A

Question 2

What is the major organic product of the following reaction?

Accepted Answer

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

Question 3

Compound X can be synthesized via a ring-closing metathesis reaction when treated with a Grubbs' catalyst. What is a possible structure of the starting material for this reaction?

Accepted Answer

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

Question 4

Which of the reactions listed below is not stereospecific?

Accepted Answer

A)  Suzuki reaction 
B)  organocuprate coupling reaction 
C)  Heck reaction 
D)  Simmons-Smith reaction 
A)  Suzuki reaction 
B)  organocuprate coupling reaction 
C)  Heck reaction 
D)  Simmons-Smith reaction

Question 5

Identify the products of the following reaction.

Accepted Answer

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

Question 6

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. 
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.

Question 7

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. 
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.

Question 8

Identify the products of the following reaction.

Accepted Answer

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

Question 9

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 
A)  I 
B)  II 
C)  III 
D)  None of the choices is correct

Question 10

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

Accepted Answer

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

Question 11

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

Accepted Answer

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

Question 12

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

Question 13

Identify the major organic 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

Why is the Grubbs catalyst synthetically important?

Accepted Answer

A)  Because it only requires dilute concentrations of the reactants. 
B)  Because it produces only stereospecific products. 
C)  Because it produces only stereoselective products. 
D)  Because it provides a synthetic pathway for ring-closing metathesis reactions. 
A)  Because it only requires dilute concentrations of the reactants. 
B)  Because it produces only stereospecific products. 
C)  Because it produces only stereoselective products. 
D)  Because it provides a synthetic pathway for ring-closing metathesis reactions.

Question 15

What is the missing reactant in the following reaction?

Accepted Answer

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

Question 16

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 bond 
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 bond

Question 17

Identify the starting material that would be used to form the following product in a ring-closing metathesis reaction utilizing a Grubbs catalyst?

Accepted Answer

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

Question 18

What would be the major organic product of the following 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 appropriate sequence of reagents that will produce the target molecule shown below from ethylbenzene?

Accepted Answer

A)  (1) HBr, H2O2; (2) KOC(CH3)3 ; (3) MCPBA; (4) CH2=CPh2 
B)  (1) NBS, hF1F1F1S1F1F1F10 ; (2) KOC(CH3)3 ; (3) CHBr3, KO(CH3)3 ; (4) a. LiCuPh2, b. H2O 
C)  (1) H2SO4(aq.), F1F1F1S1F1F1F10 ; (2) MCPBA; (3) CHBr3, KO(CH3)3 ; (4) CH2=CPh2 
D)  (1) Br2, FeBr3 ; (2) MCPBA; (3) CHBr3, KO(CH3)3 ; (4) Ph2COCl 
A)  (1) HBr, H2O2; (2) KOC(CH3)3 ; (3) MCPBA; (4) CH2=CPh2 
B)  (1) NBS, hF1F1F1S1F1F1F10 ; (2) KOC(CH3)3 ; (3) CHBr3, KO(CH3)3 ; (4) a. LiCuPh2, b. H2O 
C)  (1) H2SO4(aq.), F1F1F1S1F1F1F10 ; (2) MCPBA; (3) CHBr3, KO(CH3)3 ; (4) CH2=CPh2 
D)  (1) Br2, FeBr3 ; (2) MCPBA; (3) CHBr3, KO(CH3)3 ; (4) Ph2COCl

Question 20

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 carbene 
A)  a carbocation 
B)  a carbanion 
C)  a free radical 
D)  a carbene

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

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

What is the major organic product of the following reaction?

Compound X can be synthesized via a ring-closing metathesis reaction when treated with a Grubbs' catalyst. What is a possible structure of the starting material for this reaction?

Which of the reactions listed below is not stereospecific?

Identify the products of the following reaction.

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

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

Identify the products of the following reaction.

What is the major organic product of the following reaction?

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

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

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

Identify the major organic product of the following reaction.

Why is the Grubbs catalyst synthetically important?

What is the missing reactant in the following reaction?

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

Identify the starting material that would be used to form the following product in a ring-closing metathesis reaction utilizing a Grubbs catalyst?

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

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

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

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

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Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

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