Question 1

What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-methylbutane?

Accepted Answer

A)  weak nucleophile in a protic solvent 
B)  weak nucleophile in an aprotic solvent 
C)  strong nucleophile in a protic solvent 
D)  strong nucleophile in an aprotic solvent 
A)  weak nucleophile in a protic solvent 
B)  weak nucleophile in an aprotic solvent 
C)  strong nucleophile in a protic solvent 
D)  strong nucleophile in an aprotic solvent

Question 2

Which of the following compounds will undergo rearrangement in an SN1 reaction?

Accepted Answer

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

Question 3

What set of reaction conditions would favor an SN2 reaction on 2-bromo-3-methylbutane?

Accepted Answer

A)  weak nucleophile in a protic solvent 
B)  weak nucleophile in an aprotic solvent 
C)  strong nucleophile in a protic solvent 
D)  strong nucleophile in an aprotic solvent 
A)  weak nucleophile in a protic solvent 
B)  weak nucleophile in an aprotic solvent 
C)  strong nucleophile in a protic solvent 
D)  strong nucleophile in an aprotic solvent

Question 4

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

The answer of Provide the reagents necessary to carry out...

Question 5

Which of the following is true about the stereochemistry of SN1 reaction?

Accepted Answer

A)  retention of configuration at the electrophilic center 
B)  inversion of configuration at the electrophilic center 
C)  50:50 mixture of retention and inversion of configuration at the electrophilic center 
D)  slightly more inversion than retention at the electrophilic center 
E)  slightly more retention than inversion at the electrophilic center 
A)  retention of configuration at the electrophilic center 
B)  inversion of configuration at the electrophilic center 
C)  50:50 mixture of retention and inversion of configuration at the electrophilic center 
D)  slightly more inversion than retention at the electrophilic center 
E)  slightly more retention than inversion at the electrophilic center

Question 6

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 7

Rank the following compounds from most to least reactive in an SN1 reaction.

Accepted Answer

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

Question 8

Predict the product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these

Question 9

Which of the following is the rate equation for the following SN1 reaction?

Accepted Answer

A)  Rate = k[H2O] 
B)  Rate = k[1-chloro-1-methylcyclohexane] [H2O] 
C)  Rate = k[chloride ion] 
D)  Rate = k[1-chloro-1-methylcyclohexane] 
A)  Rate = k[H2O] 
B)  Rate = k[1-chloro-1-methylcyclohexane] [H2O] 
C)  Rate = k[chloride ion] 
D)  Rate = k[1-chloro-1-methylcyclohexane]

Question 10

Predict the product for the following SN1 reaction.

Accepted Answer

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

Question 11

Which of the following alkyl halides is essentially unreactive in an SN2 reaction?

Accepted Answer

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

Question 12

Which of the following is a primary alkyl halide?

Accepted Answer

A)  (CH3)2CHCH2Cl 
B)  (CH3)2CClCH2CH3 
C)  (CH3)2CHCHClCH3 
D)  (CH3)2CHCH2CCl(CH3)2 
A)  (CH3)2CHCH2Cl 
B)  (CH3)2CClCH2CH3 
C)  (CH3)2CHCHClCH3 
D)  (CH3)2CHCH2CCl(CH3)2

Question 13

Which of the following is a substitution reaction?

Accepted Answer

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

Question 14

Predict the major product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  Both II & III 
D)  Both I & IV 
E)  V 
A)  I 
B)  II 
C)  Both II & III 
D)  Both I & IV 
E)  V

Question 15

Which of the following is NOT a nucleophile?

Accepted Answer

A)  OH- 
B)  NH3 
C)  CH3OH 
D)  NH4+ 
E)  All of these 
A)  OH- 
B)  NH3 
C)  CH3OH 
D)  NH4+ 
E)  All of these

Question 16

What is the IUPAC name for the following compound?

Accepted Answer

1,1-dibrom

Question 17

Which of the following alkyl halides will undergo the fastest SN1 reaction?

Accepted Answer

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

Question 18

Predict the product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of these

Question 19

Predict the product for the following SN2 reaction.

Accepted Answer

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

Question 20

Which of the following alkyl halides will undergo the slowest SN1 reaction?

Accepted Answer

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

Exam 7: Substitution Reactions

What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-methylbutane?

Which of the following compounds will undergo rearrangement in an SN1 reaction?

What set of reaction conditions would favor an SN2 reaction on 2-bromo-3-methylbutane?

Provide the reagents necessary to carry out the following conversion.

Which of the following is true about the stereochemistry of SN1 reaction?

Predict the product for the following reaction.

Rank the following compounds from most to least reactive in an SN1 reaction.

Predict the product for the following reaction.

Which of the following is the rate equation for the following SN1 reaction?

Predict the product for the following SN1 reaction.

Which of the following alkyl halides is essentially unreactive in an SN2 reaction?

Which of the following is a primary alkyl halide?

Which of the following is a substitution reaction?

Predict the major product for the following reaction.

Which of the following is NOT a nucleophile?

What is the IUPAC name for the following compound?

Which of the following alkyl halides will undergo the fastest SN1 reaction?

Predict the product for the following reaction.

Predict the product for the following SN2 reaction.

Which of the following alkyl halides will undergo the slowest SN1 reaction?

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkenes: Structure and Preparation Via Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

What set of reaction conditions would favor an S_N1 reaction on 2-bromo-3-methylbutane?

Which of the following compounds will undergo rearrangement in an S_N1 reaction?

What set of reaction conditions would favor an S_N2 reaction on 2-bromo-3-methylbutane?

Which of the following is true about the stereochemistry of S_N1 reaction?

Rank the following compounds from most to least reactive in an S_N1 reaction.

Which of the following is the rate equation for the following S_N1 reaction?

Predict the product for the following S_N1 reaction.

Which of the following alkyl halides is essentially unreactive in an S_N2 reaction?

Which of the following alkyl halides will undergo the fastest S_N1 reaction?

Predict the product for the following S_N2 reaction.

Which of the following alkyl halides will undergo the slowest S_N1 reaction?