Question 1

Which of the following carbocations is the most stable?

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 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.

Question 3

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

Question 4

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 5

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

Accepted Answer

A) The reaction involves two steps and occurs fastest with primary alkyl halides. 
B) The reaction involves one step and occurs fastest with primary alkyl halides. 
C) The reaction involves one step and occurs fastest with tertiary alkyl halides. 
D) The reaction involves two steps and occurs fastest with tertiary alkyl halides. 
A) The reaction involves two steps and occurs fastest with primary alkyl halides. 
B) The reaction involves one step and occurs fastest with primary alkyl halides. 
C) The reaction involves one step and occurs fastest with tertiary alkyl halides. 
D) The reaction involves two steps and occurs fastest with tertiary alkyl halides.

Question 6

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 7

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 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

What is the IUPAC name of the following compound?

Accepted Answer

A) 2-Bromo-5-methyloctane 
B) 2-Bromo-3-methylheptane 
C) 2-Bromo-5-methylheptane 
D) 6-Bromo-3-methylheptane 
A) 2-Bromo-5-methyloctane 
B) 2-Bromo-3-methylheptane 
C) 2-Bromo-5-methylheptane 
D) 6-Bromo-3-methylheptane

Question 10

Which of the following alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br,(CH3)2CHCH2Br,CH3CH2CH(CH3)Br,(CH3)3CBr

Accepted Answer

A) CH3CH2CH2CH2Br 
B) (CH3)2CHCH2Br 
C) CH3CH2CH(CH3)Br 
D) (CH3)3CBr 
A) CH3CH2CH2CH2Br 
B) (CH3)2CHCH2Br 
C) CH3CH2CH(CH3)Br 
D) (CH3)3CBr

Question 11

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 12

Rank the following in order of increasing leaving group ability,putting the worst leaving group first.

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 13

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

Exam 7: Alkyl Halides and Nucleophilic Substitution

Which of the following carbocations is the most stable?

Which of the following statements is not true?

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

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-

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

Which of the following is the most nucleophilic?

Which of the following statements 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 alkyl halides would react the fastest with H2O in SN1 reaction? CH3CH2CH2CH2Br,(CH3)2CHCH2Br,CH3CH2CH(CH3)Br,(CH3)3CBr

Which of the following statements about SN2 reactions is true?

Rank the following in order of increasing leaving group ability,putting the worst leaving group first.

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

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

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

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^-

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

Which of the following alkyl halides would react the fastest with H₂O in S_N1 reaction? CH₃CH₂CH₂CH₂Br,(CH₃)₂CHCH₂Br,CH₃CH₂CH(CH₃)Br,(CH₃)₃CBr

Which of the following statements about S_N2 reactions is true?