Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

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Consider the reaction of (CH₃)₃CO^- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

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Question 21

Among the following alkyl halides, choose the one with the lowest boiling point.

(Multiple Choice)

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Question 22

What is the IUPAC name of the compound shown below?

(Multiple Choice)

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Question 23

Which of the following alkyl halides is most likely to undergo rearrangement in an S_N1 reaction?

(Multiple Choice)

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Question 24

Provide the structure of the major organic product in the following reaction.

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Question 25

Provide the structure of the major organic product in the following reaction.

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Question 26

Show the best way to prepare CH₃OCH(CH₃)₂ by an S_N2 reaction.

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Question 27

When ionization occurs at the single stereocenter of a chiral compound, the resulting carbocation is:

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Question 28

Provide the major organic product of the reaction below.

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Question 29

Provide an acceptable name for the compound shown below.

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Question 30

The flame retardant below has been found to be an androgen agonist and may have a contribution to an increasing rate of occurrence of prostate cancer (J. Med. Chem. 2006, 7366). What is the correct term that describes the relative position of the bromides in this structure?

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Question 31

Arrange the following species in order of increasing nucleophilicity: CH₃CH₂S^-, CH₃CH₂O^-, (CH₃)₃CO^-, (CH₃)₃COH.

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Question 32

Predict the most likely mechanism for the reaction shown below.

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Question 33

List the following bromides in order of their increasing reactivity as substrates in S_N1 reactions: 2-chlorobutane, 2-iodobutane, and 1-iodobutane.

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Question 34

Rank the species below in order of increasing nucleophilicity in hydroxylic solvents: CH₃CO₂^-, CH₃S^-, HO^-, H₂O.

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Question 35

Dehydration of 1-butanol with concentrated sulfuric acid at 140^∘C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?

(Multiple Choice)

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Question 36

Which of the following alkyl bromides undergoes solvolysis in aqueous methanol most rapidly?

(Multiple Choice)

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Question 37

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

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Question 38

Provide the major organic product of the reaction below.

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Question 39

How many distinct alkene products results when 1-bromo-1-ethylcyclopentane is treated with NaOCH₃?

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Question 40

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Exam 6: Alkyl Halides: Nucleophilic Substitution and Elimination

Consider the reaction of (CH3)3CO- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

Among the following alkyl halides, choose the one with the lowest boiling point.

What is the IUPAC name of the compound shown below?

Which of the following alkyl halides is most likely to undergo rearrangement in an SN1 reaction?

Provide the structure of the major organic product in the following reaction.

Provide the structure of the major organic product in the following reaction.

Show the best way to prepare CH3OCH(CH3)2 by an SN2 reaction.

When ionization occurs at the single stereocenter of a chiral compound, the resulting carbocation is:

Provide the major organic product of the reaction below.

Provide an acceptable name for the compound shown below.

The flame retardant below has been found to be an androgen agonist and may have a contribution to an increasing rate of occurrence of prostate cancer (J. Med. Chem. 2006, 7366). What is the correct term that describes the relative position of the bromides in this structure?

Arrange the following species in order of increasing nucleophilicity: CH3CH2S-, CH3CH2O-, (CH3)3CO-, (CH3)3COH.

Predict the most likely mechanism for the reaction shown below.

List the following bromides in order of their increasing reactivity as substrates in SN1 reactions: 2-chlorobutane, 2-iodobutane, and 1-iodobutane.

Rank the species below in order of increasing nucleophilicity in hydroxylic solvents: CH3CO2-, CH3S-, HO-, H2O.

Dehydration of 1-butanol with concentrated sulfuric acid at 140∘C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?

Which of the following alkyl bromides undergoes solvolysis in aqueous methanol most rapidly?

Name the haloalkane shown. Be sure to include the appropriate R or S description if needed.

Provide the major organic product of the reaction below.

How many distinct alkene products results when 1-bromo-1-ethylcyclopentane is treated with NaOCH3?

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Consider the reaction of (CH₃)₃CO^- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased? Explain.

Which of the following alkyl halides is most likely to undergo rearrangement in an S_N1 reaction?

Show the best way to prepare CH₃OCH(CH₃)₂ by an S_N2 reaction.

Arrange the following species in order of increasing nucleophilicity: CH₃CH₂S^-, CH₃CH₂O^-, (CH₃)₃CO^-, (CH₃)₃COH.

List the following bromides in order of their increasing reactivity as substrates in S_N1 reactions: 2-chlorobutane, 2-iodobutane, and 1-iodobutane.

Rank the species below in order of increasing nucleophilicity in hydroxylic solvents: CH₃CO₂^-, CH₃S^-, HO^-, H₂O.

Dehydration of 1-butanol with concentrated sulfuric acid at 140^∘C results in the formation of mainly trans-2-butene. According to these results, which of the following conclusions might be valid?

How many distinct alkene products results when 1-bromo-1-ethylcyclopentane is treated with NaOCH₃?