Question 1

Rank the following compounds in order of increasing SN2 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 2

What is the IUPAC name of the following compound?

Accepted Answer

A) (1R,3R)-1-bromo-3-isopropylcyclopentane 
B) (1R,3S)-1-bromo-3-isopropylcyclopentane 
C) (1S,3R)-1-bromo-3-isopropylcyclopentane 
D) (1S,3S)-1-bromo-3-isopropylcyclopentane 
A) (1R,3R)-1-bromo-3-isopropylcyclopentane 
B) (1R,3S)-1-bromo-3-isopropylcyclopentane 
C) (1S,3R)-1-bromo-3-isopropylcyclopentane 
D) (1S,3S)-1-bromo-3-isopropylcyclopentane

Question 3

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

Question 4

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 5

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 6

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 7

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

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

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

Accepted Answer

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

Question 10

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

Question 11

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 12

Rank the following halides in order of decreasing polarity,putting the most polar first.

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 13

Which of the following statements is not true?

Accepted Answer

A) In polar protic solvents,nucleophilicity decreases down a column of the periodic table as the size of the anion increases. 
B) Nucleophilicity is affected by the solvent used in a substitution reaction. 
C) Polar protic solvents are capable of intermolecular hydrogen bonding. 
D) Polar protic solvents solvate both cations and anions. 
A) In polar protic solvents,nucleophilicity decreases down a column of the periodic table as the size of the anion increases. 
B) Nucleophilicity is affected by the solvent used in a substitution reaction. 
C) Polar protic solvents are capable of intermolecular hydrogen bonding. 
D) Polar protic solvents solvate both cations and anions.

Exam 7: Alkyl Halides and Nucleophilic Substitution

Rank the following compounds in order of increasing SN2 reactivity?

What is the IUPAC name of the following compound?

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

Which of the following carbocations is the most stable?

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 about an SN1 reaction mechanism is true?

Which alkyl halide will form the most stable carbocation?

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

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

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

Rank the following halides in order of decreasing polarity,putting the most polar first.

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 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

Rank the following compounds in order of increasing S_N2 reactivity?

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

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

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