Question 1

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 A

Question 2

Which alkyl halide will form the most stable carbocation?

Accepted Answer

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

Question 3

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 B

Question 4

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 5

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 6

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 7

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 8

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 9

Identify the nucleophile and type of substitution reaction in the following:

Accepted Answer

A) CN-,Sn1 
B) CN-,Sn2 
C) Br-,Sn1 
D) Br-,Sn2 
A) CN-,Sn1 
B) CN-,Sn2 
C) Br-,Sn1 
D) Br-,Sn2

Question 10

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 11

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 12

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 13

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 14

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 15

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 16

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 17

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 18

Rank the following molecules in order of increasing polarity,putting the least polar first.

Accepted Answer

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

Question 19

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 20

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

Exam 7: Alkyl Halides and Nucleophilic Substitution

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

Which alkyl halide will form the most stable carbocation?

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

What is the starting material in the reaction shown below?

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 an SN1 reaction mechanism 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?

Identify the nucleophile and type of substitution reaction in the following:

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

What is the IUPAC name of the following compound?

What is the starting material in the reaction shown below?

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

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

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

Rank the following compounds in order of increasing SN1 reactivity?

What is the IUPAC name of the following compound?

Rank the following molecules in order of increasing polarity,putting the least polar first.

Which of the following structures have the correct common name?

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

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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

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

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

Rank the following compounds in order of increasing S_N1 reactivity?

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