Question 1

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. 
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 2

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 3

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

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

Question 6

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 7

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 8

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 9

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

Question 10

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 11

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 12

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 
A) Methane gas and nitrogen gas 
B) Propene gas and nitrogen gas 
C) Methyl radical and nitrogen gas 
D) Methylene and nitrogen gas

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

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. 
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 15

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 16

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 17

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 18

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. 
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 19

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 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

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

Identify the major organic product 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?

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

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

Identify the products of the following reaction.

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

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

Identify the major organic product of the following reaction.

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

What products are formed when diazomethane is heated?

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

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?

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

What is the major organic product of the following reaction?

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

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

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

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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

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?