Question 1

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

Question 2

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 3

Given the following substitution reaction,what would be the effect of changing the solvent from CH3OH to (CH3)2S=O? CH3(CH2)5Br + NaOH ® 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 4

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 5

Rank the alkyl halides in order of decreasing SN2 reactivity,putting the most reactive first.

Accepted Answer

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

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

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 8

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 9

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 10

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 11

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 12

Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism?

Accepted Answer

A) They don't undergo SN1 reactions because a higher percent s-character makes the bond longer and stronger. 
B) They don't undergo SN2 reactions because a higher percent s-character makes the bond shorter and stronger. 
C) They don't undergo SN2 reactions because heterolysis of the C-X bond forms a highly unstable carbocation. 
D) They don't undergo SN1 reactions because the carbocation is highly electronegative. 
A) They don't undergo SN1 reactions because a higher percent s-character makes the bond longer and stronger. 
B) They don't undergo SN2 reactions because a higher percent s-character makes the bond shorter and stronger. 
C) They don't undergo SN2 reactions because heterolysis of the C-X bond forms a highly unstable carbocation. 
D) They don't undergo SN1 reactions because the carbocation is highly electronegative.

Question 13

What is the IUPAC name of the following compound?

Accepted Answer

A) (3R,4R)-3-chloro-4-methylhexane 
B) (3R,4S)-3-chloro-4-methylhexane 
C) (3S,4R)-3-chloro-4-methylhexane 
D) (3S,4S)-3-chloro-4-methylhexane 
A) (3R,4R)-3-chloro-4-methylhexane 
B) (3R,4S)-3-chloro-4-methylhexane 
C) (3S,4R)-3-chloro-4-methylhexane 
D) (3S,4S)-3-chloro-4-methylhexane

Question 14

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 15

Which of the following statements is not true?

Accepted Answer

A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide. 
B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases. 
C) Sterically hindered bases are also called nonnucleophilic bases. 
D) Steric hindrance decreases basicity but not nucleophilicity. 
A) Sodium ethoxide is a better nucleophile than sodium tert-butoxide. 
B) Sodium tert-butoxide and sodium ethoxide have similar strengths as bases. 
C) Sterically hindered bases are also called nonnucleophilic bases. 
D) Steric hindrance decreases basicity but not nucleophilicity.

Question 16

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 17

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 18

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 19

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 20

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

Exam 7: Alkyl Halides and Nucleophilic Substitution

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

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

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

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

Rank the alkyl halides in order of decreasing SN2 reactivity,putting the most reactive first.

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

What is the starting material in the reaction shown below?

Which of the following structures have the correct common name?

Which of the following statements about SN2 reactions is true?

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

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

Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the SN1 or SN2 mechanism?

What is the IUPAC name of the following compound?

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

Which of the following statements is not true?

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

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

Rank the following compounds in order of increasing SN1 reactivity?

What is the IUPAC name of the following compound?

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

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

Rank the alkyl halides in order of decreasing S_N2 reactivity,putting the most reactive first.

Which of the following statements about S_N2 reactions is true?

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

Which of the following statements explain why aryl halides and vinyl halides do not undergo nucleophilic substitution by either the S_N1 or S_N2 mechanism?

Rank the following compounds in order of increasing S_N1 reactivity?