Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
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Chapter 9, Problem 56P

(a)

Interpretation Introduction

Interpretation:

Rate of the reaction of methyl iodide with quinuclidine and methyl iodide with trimethylamine is measured in nitrobenzene, based on it answer the following questions.

Concept Introduction:

Rateα [alkyl halide][nucleophile]

Thus,

rate=k[alkylhalide][nucleophile] , where k is the rate constant.

Increasing the height of the energy barrier decreases the magnitude of the rate constant, thus causes the reaction to be slower.

The rate of the SN2 reaction depends not only on the number of alkyl group but also on the size.

Steric hindrance decreases the rate of the reaction by increasing the energy of the transition state.

Higher the height of the energy barrier lowers the rate constant.

(b)

Interpretation Introduction

Interpretation:

Rate of the reaction of methyl iodide with quinuclidine and methyl iodide with trimethylamine is measured in nitrobenzene, based on it answer the following questions.

Concept Introduction:

Rateα [alkyl halide][nucleophile]

Thus,

rate=k[alkylhalide][nucleophile] , where k is the rate constant.

Increasing the height of the energy barrier decreases the magnitude of the rate constant, thus causes the reaction to be slower.

The rate of the SN2 reaction depends not only on the number of alkyl group but also on the size.

Steric hindrance decreases the rate of the reaction by increasing the energy of the transition state.

Higher the height of the energy barrier lowers the rate constant.

(c)

Interpretation Introduction

Interpretation:

Rate of the reaction of methyl iodide with quinuclidine and methyl iodide with trimethylamine is measured in nitrobenzene, based on it answer the following questions.

Concept Introduction:

Rateα [alkyl halide][nucleophile]

Thus,

rate=k[alkylhalide][nucleophile] , where k is the rate constant.

Increasing the height of the energy barrier decreases the magnitude of the rate constant, thus causes the reaction to be slower.

The rate of the SN2 reaction depends not only on the number of alkyl group but also on the size.

Steric hindrance decreases the rate of the reaction by increasing the energy of the transition state.

Higher the height of the energy barrier lowers the rate constant.

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The rate of the reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of the reaction of methyl iodide withtriethylamine was measured in the same solvent. The concentration of the reagents was the same in both experiments.a. Which reaction had the larger rate constant?b. The same experiment was done using isopropyl iodide instead of methyl iodide. Which reaction had the larger rate constant? c. Which alkyl halide has the larger kquinuclidine/ktriethylamine ratio?
What is the first step in the general mechanism for electrophilic aromatic substitution? a. aromatic ring protonation b.loss of the electrophilic aromatic ring c. deprotonation of the aromatic ring d.addition of the electrophilic to the aromatic ring.
How will the rate of the reaction between bromomethane and hydroxide ion be affected if the following changes in concentration are made? a. The concentration of the alkyl halide is not changed and the concentration of the nucleophile is tripled. b. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is not changed. c. The concentration of the alkyl halide is cut in half and the concentration of the nucleophile is doubled.

Chapter 9 Solutions

Organic Chemistry

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