Question 1

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 2

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 3

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

Question 4

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 5

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 6

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 7

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 8

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 9

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 10

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 11

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 12

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 13

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 14

Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion.

Accepted Answer

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

Question 15

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 16

Rank the following in order of decreasing leaving group ability, putting the best first.

Accepted Answer

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

Question 17

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 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

Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and -OCH3.

Accepted Answer

A) CH2CH2OH 
B) CH3OH 
C) DMSO 
D) H2O 
A) CH2CH2OH 
B) CH3OH 
C) DMSO 
D) H2O

Question 20

Which of the following alkyl halides would react the fastest with -OH in SN2 reaction? CH3CH2Br, CH3CH2Cl, CH3CH2F, CH3CH2I

Accepted Answer

A) CH3CH2Br 
B) CH3CH2Cl 
C) CH3CH2F 
D) CH3CH2I 
A) CH3CH2Br 
B) CH3CH2Cl 
C) CH3CH2F 
D) CH3CH2I

Exam 7: Alkyl Halides and Nucleophilic Substitution

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 structures have the correct common name?

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.

Which of the following is the most nucleophilic?

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

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

What is the IUPAC name of the following compound?

Which of the following is a polar aprotic solvent?

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

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

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

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

Rank the following ions in order of increasing nucleophilicity in polar protic solvents, starting with the least nucleophilic ion.

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

Rank the following in order of decreasing leaving group ability, putting the best first.

What is the IUPAC name of the following compound?

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

Pick the solvent that gives the fastest SN2 reaction between CH2CH2Br and -OCH3.

Which of the following alkyl halides would react the fastest with -OH in SN2 reaction? CH3CH2Br, CH3CH2Cl, CH3CH2F, CH3CH2I

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

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

Pick the solvent that gives the fastest S_N2 reaction between CH₂CH₂Br and ^-OCH₃.

Which of the following alkyl halides would react the fastest with ^-OH in S_N2 reaction? CH₃CH₂Br, CH₃CH₂Cl, CH₃CH₂F, CH₃CH₂I