Question 1

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. D

Question 2

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. A

Question 3

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 D

Question 4

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 5

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 6

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 7

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 8

Given the following substitution reaction, what would the effect be of changing the solvent from CH3OH to (CH3)2S=O? CH3(CH2)5Br + NaOH F1F1F1S1F1F1F10 CH3(CH2)5OH + Br-

Accepted Answer

A)  The rate would decrease because SN1 reactions are favored by polar protic solvents. 
B)  The rate would increase because SN2 reactions are favored by polar aprotic solvents. 
C)  The rate would increase because SN1 reactions are favored by polar protic solvents. 
D)  The rate would decrease because SN2 reactions are favored by polar aprotic solvents. 
A)  The rate would decrease because SN1 reactions are favored by polar protic solvents. 
B)  The rate would increase because SN2 reactions are favored by polar aprotic solvents. 
C)  The rate would increase because SN1 reactions are favored by polar protic solvents. 
D)  The rate would decrease because SN2 reactions are favored by polar aprotic solvents.

Question 9

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 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

What is the IUPAC name of the following compound?

Accepted Answer

A)  (
E) -2-Bromo-3,4-dimethyl-2-pentene 
B)  (Z)-1-Bromo-1,2,3-trimethyl-1-butene 
C)  (Z)-2-Bromo-3,4-dimethyl-2-pentene 
D)  (
E) -1-Bromo-1,2,3-trimethyl-1-butene 
A)  (
E) -2-Bromo-3,4-dimethyl-2-pentene 
B)  (Z)-1-Bromo-1,2,3-trimethyl-1-butene 
C)  (Z)-2-Bromo-3,4-dimethyl-2-pentene 
D)  (
E) -1-Bromo-1,2,3-trimethyl-1-butene

Question 12

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 13

Which of the following alkyl halides will react fastest with CH3OH in an SN1 mechanism?

Accepted Answer

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

Question 14

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 15

What is the IUPAC name of the following compound?

Accepted Answer

A)  (R)-3-Bromo-1-methylcyclohexene 
B)  (S)-3-Bromo-1-methylcyclohexene 
C)  (S)-1-Bromo-3-methyl-2-cyclohexene 
D)  (R)-1-Bromo-3-methyl-2-cyclohexene 
A)  (R)-3-Bromo-1-methylcyclohexene 
B)  (S)-3-Bromo-1-methylcyclohexene 
C)  (S)-1-Bromo-3-methyl-2-cyclohexene 
D)  (R)-1-Bromo-3-methyl-2-cyclohexene

Question 16

Which of the following solvents is not a polar protic solvent? $$\begin{array} { c c c c } 
\mathrm { CH } _ { 3 } \mathrm { OH } & \mathrm { CH } _ { 3 } \mathrm { CN } & \mathrm { CH } _ { 3 } \mathrm { COOH } & \mathrm { H } _ { 2 } \mathrm { O } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

Accepted Answer

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

Question 17

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 18

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 19

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 20

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

Exam 7: Alkyl Halides and Nucleophilic Substitution

Which of the following statements about carbocation stability is true?

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

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

Which of the following statements about SN2 reactions is true?

Which of the following structures have the correct common name?

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

Which of the following is the most nucleophilic?

Given the following substitution reaction, what would the effect be of changing the solvent from CH3OH to (CH3)2S=O? CH3(CH2)5Br + NaOH  CH3(CH2)5OH + Br-

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

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

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

Which of the following alkyl halides will react fastest with CH3OH in an SN1 mechanism?

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

Which of the following solvents is not a polar protic solvent? I II III IV

Which of the following structures have the correct common name?

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

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?

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

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 Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

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

Lipids

Synthetic Polymers

Filters

Which of the following statements about S_N2 reactions is true?

Given the following substitution reaction, what would the effect be of changing the solvent from CH₃OH to (CH₃)₂S=O? CH₃(CH₂)₅Br + NaOH  CH₃(CH₂)₅OH + Br^-

Which of the following alkyl halides will react fastest with CH₃OH in an S_N1 mechanism?