Question 1

Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first.

Accepted Answer

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

Question 2

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] A

Question 3

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

Accepted Answer

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

Question 4

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 5

What is the IUPAC name of the following compound?

Accepted Answer

A) 2-Bromo-5-methyloctane 
B) 2-Bromo-3-methylheptane 
C) 2-Bromo-5-methylheptane 
D) 6-Bromo-3-methylheptane 
A) 2-Bromo-5-methyloctane 
B) 2-Bromo-3-methylheptane 
C) 2-Bromo-5-methylheptane 
D) 6-Bromo-3-methylheptane

Question 6

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 7

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 8

What is the IUPAC name of the following compound?

Accepted Answer

A) 2-Chloro-4-isopropyl-2,6-dimethyloctane 
B) 2-Chloro-4-isopropyl-2,7-dimethylnonane 
C) 2,6-Dimethyl-2-chloro-4-isopropyloctane 
D) 7-Chloro-5-isopropyl-3,7-dimethyloctane 
A) 2-Chloro-4-isopropyl-2,6-dimethyloctane 
B) 2-Chloro-4-isopropyl-2,7-dimethylnonane 
C) 2,6-Dimethyl-2-chloro-4-isopropyloctane 
D) 7-Chloro-5-isopropyl-3,7-dimethyloctane

Question 9

Rank the following compounds in order of increasing SN1 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 10

Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br, (CH3)2CHCH2Br, CH3CH2CH(CH3)Br, (CH3)3CBr

Accepted Answer

A) CH3CH2CH2CH2Br 
B) (CH3)2CHCH2Br 
C) CH3CH2CH(CH3)Br 
D) (CH3)3CBr 
A) CH3CH2CH2CH2Br 
B) (CH3)2CHCH2Br 
C) CH3CH2CH(CH3)Br 
D) (CH3)3CBr

Question 11

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 12

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 13

What is the IUPAC name of the following compound?

Accepted Answer

A) (R)-3-Chloro-6-ethyloctane 
B) (S)-3-Chloro-6-ethyloctane 
C) (S)-6-Chloro-3-ethyloctane 
D) (R)-6-Chloro-3-ethyloctane 
A) (R)-3-Chloro-6-ethyloctane 
B) (S)-3-Chloro-6-ethyloctane 
C) (S)-6-Chloro-3-ethyloctane 
D) (R)-6-Chloro-3-ethyloctane

Question 14

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 15

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 16

Which of the following statements is not true?

Accepted Answer

A) In polar protic solvents, nucleophilicity decreases down a column of the periodic table as the size of the anion increases. 
B) Nucleophilicity is affected by the solvent used in a substitution reaction. 
C) Polar protic solvents are capable of intermolecular hydrogen bonding. 
D) Polar protic solvents solvate both cations and anions. 
A) In polar protic solvents, nucleophilicity decreases down a column of the periodic table as the size of the anion increases. 
B) Nucleophilicity is affected by the solvent used in a substitution reaction. 
C) Polar protic solvents are capable of intermolecular hydrogen bonding. 
D) Polar protic solvents solvate both cations and anions.

Question 17

Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic first.

Accepted Answer

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

Question 18

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 19

Which of the following statements about SN2 reactions is true?

Accepted Answer

A) The rate of reaction is dependent on just the substrate. 
B) The fastest reaction will occur with a tertiary alkyl halide. 
C) The mechanism is a two-step process. 
D) Displacement occurs with inversion of configuration. 
A) The rate of reaction is dependent on just the substrate. 
B) The fastest reaction will occur with a tertiary alkyl halide. 
C) The mechanism is a two-step process. 
D) Displacement occurs with inversion of configuration.

Question 20

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

Accepted Answer

A) The reaction involves two steps and occurs fastest with primary alkyl halides. 
B) The reaction involves one step and occurs fastest with primary alkyl halides. 
C) The reaction involves one step and occurs fastest with tertiary alkyl halides. 
D) The reaction involves two steps and occurs fastest with tertiary alkyl halides. 
A) The reaction involves two steps and occurs fastest with primary alkyl halides. 
B) The reaction involves one step and occurs fastest with primary alkyl halides. 
C) The reaction involves one step and occurs fastest with tertiary alkyl halides. 
D) The reaction involves two steps and occurs fastest with tertiary alkyl halides.

Exam 7: Alkyl Halides and Nucleophilic Substitution

Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first.

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

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

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

What is the IUPAC name of the following compound?

Which of the following statements is true?

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?

What is the IUPAC name of the following compound?

Rank the following compounds in order of increasing SN1 reactivity?

Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br, (CH3)2CHCH2Br, CH3CH2CH(CH3)Br, (CH3)3CBr

What is the starting material in the reaction shown below?

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

What is the IUPAC name of the following compound?

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

Which of the following structures have the correct common name?

Which of the following statements is not true?

Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic first.

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 SN2 reactions is true?

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

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

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Filters

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

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

Rank the following compounds in order of increasing S_N1 reactivity?

Which of the following alkyl halides would react the fastest with H₂O in S_N1 reaction? CH₃CH₂CH₂CH₂Br, (CH₃)₂CHCH₂Br, CH₃CH₂CH(CH₃)Br, (CH₃)₃CBr

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 S_N2 reactions is true?

Which of the following statements about an S_N1 reaction mechanism is true?