Question 1

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 2

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

Accepted Answer

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

Question 3

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 4

Rank the following molecules in order of increasing polarity, putting the least polar first. $$\begin{array} { c c c c } 
\mathrm { CH } _ { 4 } & \mathrm { CH } _ { 3 } \mathrm { Cl } & \mathrm { CH } _ { 3 } \mathrm { Br } & \mathrm { CH } _ { 3 } \mathrm { I } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

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 5

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 6

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 7

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 8

Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first. $$\begin{array} { c c c c } 
\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { O } ^ { - } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm {~S} ^ { - } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { OH } & \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { SH } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

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

Question 9

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 10

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]

Question 11

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, CH3OH 
B)  SN1, DMSO 
C)  SN2, CH3OH 
D)  SN2, DMSO 
A)  SN1, CH3OH 
B)  SN1, DMSO 
C)  SN2, CH3OH 
D)  SN2, DMSO

Question 12

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 13

Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic first. $$\begin{array} { c c c c } 
\mathrm { CH } _ { 3 } \mathrm { OH } & \mathrm { CH } _ { 3 } \mathrm { O } ^ { - } & \mathrm { CH } _ { 3 } \mathrm {~S} ^ { - } & \mathrm { CH } _ { 3 } \mathrm { SH } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

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 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 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 16

What is the rate-determining step of an SN1 reaction mechanism?

Accepted Answer

A)  Reaction of the nucleophile with the carbocation to form the product. 
B)  Breaking the bond between the carbon and the leaving group to generate a carbocation. 
C)  Attack of the nucleophile on the substrate to generate a pentavalent carbon. 
D)  None of the above. 
A)  Reaction of the nucleophile with the carbocation to form the product. 
B)  Breaking the bond between the carbon and the leaving group to generate a carbocation. 
C)  Attack of the nucleophile on the substrate to generate a pentavalent carbon. 
D)  None of the above.

Question 17

Rank the following in order of increasing leaving group ability, putting the worst leaving group first. $$\begin{array} { c c c c } 
\mathrm { H } _ { 2 } \mathrm { O } & \mathrm { HO } ^ { - } & \mathrm { NH } _ { 3 } & \mathrm { H } _ { 2 } \mathrm {~N} ^ { - } \
\text {I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

Accepted Answer

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

Question 18

Rank the following halides in order of decreasing polarity, putting the most polar first. $$\begin{array} { c c c c } 
\mathrm { CCl } _ { 4 } & \mathrm { CHCl } _ { 3 } & \mathrm { CH } _ { 2 } \mathrm { Cl } _ { 2 } & \mathrm { CH } _ { 3 } \mathrm { Cl } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

Accepted Answer

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

Question 19

Which of the following is not a characteristic of an SN1 reaction?

Accepted Answer

A)  The rate is proportional to the concentration of substrate. 
B)  The reaction is favored in polar protic solvents. 
C)  The rate is independent of the concentration of the nucleophile. 
D)  The electrophilic carbon undergoes inversion of stereochemistry. 
A)  The rate is proportional to the concentration of substrate. 
B)  The reaction is favored in polar protic solvents. 
C)  The rate is independent of the concentration of the nucleophile. 
D)  The electrophilic carbon undergoes inversion of stereochemistry.

Question 20

Which of the following statements is not true?

Accepted Answer

A)  All good leaving groups are weak bases with strong conjugate acids. 
B)  Left-to-right across a row of the periodic table, leaving group ability increases. 
C)  Down a column of the periodic table, leaving group ability increases. 
D)  Equilibrium favors the products of the nucleophilic substitution when the leaving group is a stronger base than the nucleophile. 
A)  All good leaving groups are weak bases with strong conjugate acids. 
B)  Left-to-right across a row of the periodic table, leaving group ability increases. 
C)  Down a column of the periodic table, leaving group ability increases. 
D)  Equilibrium favors the products of the nucleophilic substitution when the leaving group is a stronger base than the nucleophile.

Exam 7: Alkyl Halides and Nucleophilic Substitution

What is the starting material in the reaction shown below?

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

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

Rank the following molecules in order of increasing polarity, putting the least polar first. I II III IV

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

Which of the following structures have the correct common name?

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

Rank the following in order of increasing nucleophilicity, putting the least nucleophilic first. I II III IV

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

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

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 statements is true?

Rank the following in order of decreasing nucleophilicity, putting the most nucleophilic first. I II III IV

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

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

What is the rate-determining step of an SN1 reaction mechanism?

Rank the following in order of increasing leaving group ability, putting the worst leaving group first. I II III IV

Rank the following halides in order of decreasing polarity, putting the most polar first. I II III IV

Which of the following is not a characteristic of an SN1 reaction?

Which of the following statements is not 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 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 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 alkyl halides in order of decreasing S_N2 reactivity, putting the most reactive first.

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

What is the rate-determining step of an S_N1 reaction mechanism?

Which of the following is not a characteristic of an S_N1 reaction?