Question 1

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 2

Which of the following is not a characteristic of an SN1 reaction?

Accepted Answer

A) The rate is proportional to the concentration of substrate. 
B) The reaction is favored in polar protic solvents. 
C) The rate is independent of the concentration of the nucleophile. 
D) The electrophilic carbon undergoes inversion of stereochemistry. 
A) The rate is proportional to the concentration of substrate. 
B) The reaction is favored in polar protic solvents. 
C) The rate is independent of the concentration of the nucleophile. 
D) The electrophilic carbon undergoes inversion of stereochemistry.

Question 3

Which of the following statements about the reactions of alkyl halides is true?

Accepted Answer

A) The characteristic reactions of alkyl halides are addition and elimination. 
B) The characteristic reactions of alkyl halides are addition and substitution. 
C) The characteristic reactions of alkyl halides are elimination and substitution. 
D) The characteristic reactions of alkyl halides are oxidation and reduction. 
A) The characteristic reactions of alkyl halides are addition and elimination. 
B) The characteristic reactions of alkyl halides are addition and substitution. 
C) The characteristic reactions of alkyl halides are elimination and substitution. 
D) The characteristic reactions of alkyl halides are oxidation and reduction.

Question 4

Which of the following structures have the correct common name?

Accepted Answer

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

Question 5

Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true?

Accepted Answer

A) Involves one step and occurs with retention of configuration. 
B) Involves two steps and occurs with inversion of configuration. 
C) Involves one step and occurs with inversion of configuration. 
D) Involves one step and occurs with racemization. 
A) Involves one step and occurs with retention of configuration. 
B) Involves two steps and occurs with inversion of configuration. 
C) Involves one step and occurs with inversion of configuration. 
D) Involves one step and occurs with racemization.

Question 6

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 7

Which of the following statements is true?

Accepted Answer

A) All good leaving groups are strong bases with weak conjugate acids. 
B) Left-to-right across a row of the periodic table,leaving group ability decreases. 
C) Down a column of the periodic table,leaving group ability decreases. 
D) The conjugate bases of strong acids are good leaving groups. 
A) All good leaving groups are strong bases with weak conjugate acids. 
B) Left-to-right across a row of the periodic table,leaving group ability decreases. 
C) Down a column of the periodic table,leaving group ability decreases. 
D) The conjugate bases of strong acids are good leaving groups.

Question 8

Which of the following anions is the most nucleophilic in polar aprotic solvents?

Accepted Answer

A) F- 
B) Cl- 
C) Br- 
D) I- 
A) F- 
B) Cl- 
C) Br- 
D) I-

Question 9

Which compound is most likely to follow second-order kinetics in a substitution reaction?

Accepted Answer

A) CH3Br 
B) (CH3)3CCH2Br 
C) CH3CH2Br 
D) (CH3)2CHBr 
A) CH3Br 
B) (CH3)3CCH2Br 
C) CH3CH2Br 
D) (CH3)2CHBr

Question 10

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 11

Which of the following statements about an SN1 reaction mechanism is true?

Accepted Answer

A) The reaction is fastest with primary alkyl halide. 
B) The reaction exhibits a one-step mechanism. 
C) The reaction rate increases as the leaving group ability increases. 
D) The reaction rate increases as the strength of the nucleophile increases. 
A) The reaction is fastest with primary alkyl halide. 
B) The reaction exhibits a one-step mechanism. 
C) The reaction rate increases as the leaving group ability increases. 
D) The reaction rate increases as the strength of the nucleophile increases.

Question 12

Rank the following carbocations in order of decreasing stability,putting the most stable first.

Accepted Answer

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

Question 13

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 14

Which of the following is the most nucleophilic?

Accepted Answer

A) CH4 
B) H2O 
C) NH3 
D) HF 
A) CH4 
B) H2O 
C) NH3 
D) HF

Question 15

The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate.What is the effect of doubling the concentration of sodium acetate on the rate of the reaction?

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 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 17

What is the starting material in the reaction shown below?

Accepted Answer

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

Question 18

Which of the following statements about the Hammond postulate is not true?

Accepted Answer

A) The Hammond postulate provides a quantitative estimate of the energy of a transition state. 
B) In endothermic reactions,the transition state is closer in energy to the products. 
C) In exothermic reactions,the transition state is closer in energy to the reactants. 
D) The Hammond postulate provides a qualitative estimate of the energy of a transition state. 
A) The Hammond postulate provides a quantitative estimate of the energy of a transition state. 
B) In endothermic reactions,the transition state is closer in energy to the products. 
C) In exothermic reactions,the transition state is closer in energy to the reactants. 
D) The Hammond postulate provides a qualitative estimate of the energy of a transition state.

Question 19

Which of the following solvents is not a polar protic solvent?

Accepted Answer

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

Question 20

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.

Exam 7: Alkyl Halides and Nucleophilic Substitution

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

Which of the following is not a characteristic of an SN1 reaction?

Which of the following statements about the reactions of alkyl halides is true?

Which of the following structures have the correct common name?

Which of the following statements about the SN2 mechanism for nucleophilic substitution reactions is true?

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 statements is true?

Which of the following anions is the most nucleophilic in polar aprotic solvents?

Which compound is most likely to follow second-order kinetics in a substitution reaction?

What is the IUPAC name of the following compound?

Which of the following statements about an SN1 reaction mechanism is true?

Rank the following carbocations in order of decreasing stability,putting the most stable first.

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

Which of the following is the most nucleophilic?

The reaction of bromoethane with sodium acetate affords the substitution product methyl acetate.What is the effect of doubling the concentration of sodium acetate on the rate of the reaction?

Which of the following statements about carbocation stability is true?

What is the starting material in the reaction shown below?

Which of the following statements about the Hammond postulate is not true?

Which of the following solvents is not a polar protic solvent?

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?

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

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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

Which of the following is not a characteristic of an S_N1 reaction?

Which of the following statements about the S_N2 mechanism for nucleophilic substitution reactions is true?

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 statements about an S_N1 reaction mechanism is true?