Exam 9: Substitution Reactions of Alkyl Halides

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Consider the following reaction mechanism: What effect will the following have on the rate? a. addition of Br^- b. using a more polar solvent c. using a stronger nucleophile d. using a more concentrated nucleophile

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Question 1

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a. reaction will slow down because of competition with Nu^-
b. reaction will speed up because a more polar solvent assists in ionization and the formation of the carbocation
c. no effect on S_N1 reactions
d. no effect on S_N1 reactions

Identify the alkyl halide that reacts the fastest in a S_N2 reaction.

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Question 2

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Which of the following solvents is protic?

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Question 3

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Which of the following S_N2 reactions is the fastest?

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Question 4

Which halide reacts most rapidly via an S_N2 mechanism?

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Question 5

Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

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Question 6

Which of the following alkyl halides gives the fastest S_N1 reaction?

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Question 7

Give the product(s)for the reaction of (R)-2-bromopentane with methanol. A)(S)-2-methoxypentane B)(R)-2-methoxypentane C)(S)-2-ethoxypentane D)(R)-2-ethoxypentane E)(R)-2-pentanol

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Question 8

Draw and describe the transition state in the S_N2 reaction between CH₃I and CH₃CH₂O^-Na⁺.

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Question 9

In each of the pairs below, which is the best nucleophile in alcoholic solvents? a. CH₃S^- or CH₃O^- ^{b. (CH}₃⁾₂NH or (CH₃⁾₃^N ^{c. Cl- or}^F- ^{d. SCN- or OCN-}

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Question 10

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

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Question 11

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

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Question 12

Provide the major organic products(s)of the reaction shown:.

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Question 13

Why, in a polar protic solvent, is iodide a better nucleophile than fluoride?

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Question 14

Give the mechanism of the reaction shown below.

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Question 15

Provide the major organic product(s)of the reaction shown

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Question 16

Which of the following compounds will undergo an S_N2 reaction most readily?

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Question 17

Which of the following alkyl halides gives the fastest S_N1 reaction?

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Question 18

Provide the structure of the major organic products which result in the reaction below.

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Question 19

S_N1 reactions usually proceed with ________.

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Question 20

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Exam 9: Substitution Reactions of Alkyl Halides

Consider the following reaction mechanism: What effect will the following have on the rate? a. addition of Br- b. using a more polar solvent c. using a stronger nucleophile d. using a more concentrated nucleophile

Identify the alkyl halide that reacts the fastest in a SN2 reaction.

Which of the following solvents is protic?

Which of the following SN2 reactions is the fastest?

Which halide reacts most rapidly via an SN2 mechanism?

Which of the compounds below undergoes solvolysis in aqueous ethanol most rapidly?

Which of the following alkyl halides gives the fastest SN1 reaction?

Give the product(s)for the reaction of (R)-2-bromopentane with methanol. A)(S)-2-methoxypentane B)(R)-2-methoxypentane C)(S)-2-ethoxypentane D)(R)-2-ethoxypentane E)(R)-2-pentanol

Draw and describe the transition state in the SN2 reaction between CH3I and CH3CH2O-Na+.

In each of the pairs below, which is the best nucleophile in alcoholic solvents? a. CH3S- or CH3O- b. (CH3)2NH or (CH3)3N c. Cl- or F- d. SCN- or OCN-

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

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

Provide the major organic products(s)of the reaction shown:.

Why, in a polar protic solvent, is iodide a better nucleophile than fluoride?

Give the mechanism of the reaction shown below.

Provide the major organic product(s)of the reaction shown

Which of the following compounds will undergo an SN2 reaction most readily?

Which of the following alkyl halides gives the fastest SN1 reaction?

Provide the structure of the major organic products which result in the reaction below.

SN1 reactions usually proceed with ________.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, Radicals

Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Alpha Carbon of Carbonyl Compounds

Reactions of Benzene and Substituted Benzenes

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

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Consider the following reaction mechanism: What effect will the following have on the rate? a. addition of Br^- b. using a more polar solvent c. using a stronger nucleophile d. using a more concentrated nucleophile

Identify the alkyl halide that reacts the fastest in a S_N2 reaction.

Which of the following S_N2 reactions is the fastest?

Which halide reacts most rapidly via an S_N2 mechanism?

Which of the following alkyl halides gives the fastest S_N1 reaction?

Draw and describe the transition state in the S_N2 reaction between CH₃I and CH₃CH₂O^-Na⁺.

In each of the pairs below, which is the best nucleophile in alcoholic solvents? a. CH₃S^- or CH₃O^- ^{b. (CH}₃⁾₂NH or (CH₃⁾₃^N ^{c. Cl- or}^F- ^{d. SCN- or OCN-}

Which of the following compounds will undergo an S_N2 reaction most readily?

Which of the following alkyl halides gives the fastest S_N1 reaction?

S_N1 reactions usually proceed with ________.