Question 1

What is the product of the nucleophilic substitution reaction shown below?

Accepted Answer

A) Only I 
B) Only II 
C) I and II 
D) None 
A) Only I 
B) Only II 
C) I and II 
D) None

Question 2

Which of the following is a polar aprotic solvent?

Accepted Answer

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

Question 3

Which of the following alkyl halides is a vinyl alkyl halide?

Accepted Answer

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

Question 4

The reaction of tert-butyl bromide,(CH3)3CBr,with ethanol affords the substitution product tert-butyl ethyl ether,(CH3)3COCH2CH3,in acidic conditions.What would happen to the rate of the reaction if the concentration of ethanol was doubled?

Accepted Answer

A) The rate remains the same. 
B) The rate decreases by a factor of 2. 
C) The rate increases by a factor of 2. 
D) The rate increases by a factor of 4. 
A) The rate remains the same. 
B) The rate decreases by a factor of 2. 
C) The rate increases by a factor of 2. 
D) The rate increases by a factor of 4.

Question 5

What is the IUPAC name of the following compound?

Accepted Answer

A) 2-Bromo-5,5-dimethylheptane 
B) 3,3-Dimethyl-6-bromoheptane 
C) 6-Bromo-3,3-dimethylheptane 
D) 2-Bromo-5,5-dimethyloctane 
A) 2-Bromo-5,5-dimethylheptane 
B) 3,3-Dimethyl-6-bromoheptane 
C) 6-Bromo-3,3-dimethylheptane 
D) 2-Bromo-5,5-dimethyloctane

Question 6

For the following reaction,use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.

Accepted Answer

A) SN1,H2O 
B) SN1,DMF 
C) SN2,H2O 
D) SN2,DMF 
A) SN1,H2O 
B) SN1,DMF 
C) SN2,H2O 
D) SN2,DMF

Question 7

What is the IUPAC name of the following compound?

Accepted Answer

A) 2-Methyl-4-chloropentane 
B) 2-Chloro-4-methylpentane 
C) 2-Chloro-1-isopropylpropane 
D) 2-Chloro-2-methylpentane 
A) 2-Methyl-4-chloropentane 
B) 2-Chloro-4-methylpentane 
C) 2-Chloro-1-isopropylpropane 
D) 2-Chloro-2-methylpentane

Question 8

Which of the following statements about the Hammond postulate is true?

Accepted Answer

A) In an exothermic reaction,lowering the energy of the transition state increases the activation energy,Ea. 
B) In an endothermic reaction,the more stable product forms faster. 
C) In an endothermic reaction,the less stable product forms faster. 
D) In an endothermic reaction,the activation energy,Ea,is similar for both products. 
A) In an exothermic reaction,lowering the energy of the transition state increases the activation energy,Ea. 
B) In an endothermic reaction,the more stable product forms faster. 
C) In an endothermic reaction,the less stable product forms faster. 
D) In an endothermic reaction,the activation energy,Ea,is similar for both products.

Question 9

The reaction of what nucleophile and substrate is represented by the following transition state?

Accepted Answer

A) Methanol with 2-bromopropane 
B) Methoxide with 2-bromopropane 
C) Methoxide with 1-bromopropane 
D) Methanol with 1-bromopropane 
A) Methanol with 2-bromopropane 
B) Methoxide with 2-bromopropane 
C) Methoxide with 1-bromopropane 
D) Methanol with 1-bromopropane

Question 10

Which of the following alkyl halides is a tertiary alkyl halide?

Accepted Answer

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

Question 11

Which of the following rate laws describes the kinetics of an SN1 reaction?

Accepted Answer

A) Rate = k[alkyl halide] 
B) Rate = k[alkyl halide][nucleophile] 
C) Rate = k[nucleophile] 
D) Rate = k[solvent] 
A) Rate = k[alkyl halide] 
B) Rate = k[alkyl halide][nucleophile] 
C) Rate = k[nucleophile] 
D) Rate = k[solvent]

Question 12

What is the rate-determining step of an SN1 reaction mechanism?

Accepted Answer

A) Reaction of the nucleophile with the carbocation to form the product. 
B) Breaking the bond between the carbon and the leaving group to generate a carbocation. 
C) Attack of the nucleophile on the substrate to generate a pentavalent carbon. 
D) None of these. 
A) Reaction of the nucleophile with the carbocation to form the product. 
B) Breaking the bond between the carbon and the leaving group to generate a carbocation. 
C) Attack of the nucleophile on the substrate to generate a pentavalent carbon. 
D) None of these.

Question 13

Which of the following structures have the correct common name?

Accepted Answer

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

Question 14

What is the IUPAC name of the following compound?

Accepted Answer

A) trans-4-Methylcyclohexyl chloride 
B) trans-p-Chloromethylcyclohexane 
C) trans-4-Methyl-1-chlorocyclohexane 
D) trans-1-Chloro-4-methylcyclohexane 
A) trans-4-Methylcyclohexyl chloride 
B) trans-p-Chloromethylcyclohexane 
C) trans-4-Methyl-1-chlorocyclohexane 
D) trans-1-Chloro-4-methylcyclohexane

Question 15

The reaction of 1-bromobutane with sodium hydroxide affords the substitution product 1-butanol.What would happen to the rate of the reaction if the concentration of both 1-bromobutane and sodium hydroxide were doubled?

Accepted Answer

A) The rate remains the same. 
B) The rate decreases by a factor of 2. 
C) The rate increases by a factor of 2. 
D) The rate increases by a factor of 4. 
A) The rate remains the same. 
B) The rate decreases by a factor of 2. 
C) The rate increases by a factor of 2. 
D) The rate increases by a factor of 4.

Question 16

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium hydroxide?

Accepted Answer

A) 1-Iodobutane 
B) 1-Chlorobutane 
C) 1-Fluorobutane 
D) 1-Bromobutane 
A) 1-Iodobutane 
B) 1-Chlorobutane 
C) 1-Fluorobutane 
D) 1-Bromobutane

Question 17

For the following reaction,use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.

Accepted Answer

A) SN1,CH3OH 
B) SN1,HMPA 
C) SN2,CH3OH 
D) SN2,HMPA 
A) SN1,CH3OH 
B) SN1,HMPA 
C) SN2,CH3OH 
D) SN2,HMPA

Question 18

Rank the following compounds in order of increasing SN2 reactivity?

Accepted Answer

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

Question 19

Which of the following statements about carbocation stability is true?

Accepted Answer

A) Carbocations are stabilized by electron-withdrawing inductive effects only. 
B) Carbocations are stabilized by electron-withdrawing inductive effects and hyperconjugation. 
C) Carbocations are stabilized by electron-donating inductive effects only. 
D) Carbocations are stabilized by electro-donating inductive effects and hyperconjugation. 
A) Carbocations are stabilized by electron-withdrawing inductive effects only. 
B) Carbocations are stabilized by electron-withdrawing inductive effects and hyperconjugation. 
C) Carbocations are stabilized by electron-donating inductive effects only. 
D) Carbocations are stabilized by electro-donating inductive effects and hyperconjugation.

Question 20

Which of the following structures have the correct common name?

Accepted Answer

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

Exam 7: Alkyl Halides and Nucleophilic Substitution

What is the product of the nucleophilic substitution reaction shown below?

Which of the following is a polar aprotic solvent?

Which of the following alkyl halides is a vinyl alkyl halide?

The reaction of tert-butyl bromide,(CH3)3CBr,with ethanol affords the substitution product tert-butyl ethyl ether,(CH3)3COCH2CH3,in acidic conditions.What would happen to the rate of the reaction if the concentration of ethanol was doubled?

What is the IUPAC name of the following compound?

For the following reaction,use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.

What is the IUPAC name of the following compound?

Which of the following statements about the Hammond postulate is true?

The reaction of what nucleophile and substrate is represented by the following transition state?

Which of the following alkyl halides is a tertiary alkyl halide?

Which of the following rate laws describes the kinetics of an SN1 reaction?

What is the rate-determining step of an SN1 reaction mechanism?

Which of the following structures have the correct common name?

What is the IUPAC name of the following compound?

The reaction of 1-bromobutane with sodium hydroxide affords the substitution product 1-butanol.What would happen to the rate of the reaction if the concentration of both 1-bromobutane and sodium hydroxide were doubled?

Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium hydroxide?

For the following reaction,use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs.Then determine which solvent affords the faster reaction.

Rank the following compounds in order of increasing SN2 reactivity?

Which of the following statements about carbocation stability is true?

Which of the following structures have the correct common name?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

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

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

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

The reaction of tert-butyl bromide,(CH₃)₃CBr,with ethanol affords the substitution product tert-butyl ethyl ether,(CH₃)₃COCH₂CH₃,in acidic conditions.What would happen to the rate of the reaction if the concentration of ethanol was doubled?

Which of the following rate laws describes the kinetics of an S_N1 reaction?

What is the rate-determining step of an S_N1 reaction mechanism?

Which of the following alkyl halides undergoes the fastest S_N2 reaction with sodium hydroxide?

Rank the following compounds in order of increasing S_N2 reactivity?