Question 1

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 2

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 3

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.

Question 4

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

Question 5

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 6

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 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 halides 
A) 1° Alkyl halides 
B) 3° Alkyl halides 
C) Vinyl halides 
D) Aryl halides

Question 8

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

Question 9

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

Question 10

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

Question 13

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 14

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 15

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 16

What is the major product of the following reaction?

Accepted Answer

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

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

Question 18

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,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 
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

Question 19

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

Accepted Answer

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

Question 20

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

Accepted Answer

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

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

Identify the major organic product of the following reaction.

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

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

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

Identify the products of the following reaction.

What is the major organic product of the following reaction?

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

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?

What is the major organic product of the following reaction?

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

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

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

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

Which of the reactions listed below is not stereospecific?

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

What is the major product of the following reaction?

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

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

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

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

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 Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

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