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The reaction of an amine with an alkyl halide gives an

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Problem 69SP Chapter 6

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 69SP

The reaction of an amine with an alkyl halide gives an ammonium salt.

The rate of this SN2 reaction is sensitive to the polarity of the solvent. Draw an energy diagram for this reaction in a nonpolar solvent and another in a polar solvent. Consider the nature of the transition state, and explain why this reaction should be sensitive to the polarity of the solvent. Predict whether it will be faster or slower in a more polar solvent.

Step-by-Step Solution:

Solution 69SP :

Step 1:

Given reaction :

The reaction of an amine with an alkyl halide gives an ammonium salt.

The rate of this SN2 reaction is sensitive to the polarity of the solvent.

Here, we have to draw an energy diagram for the above reaction in a nonpolar solvent and another energy diagram in a polar solvent. And we need to explain why this reaction should be sensitive to the polarity of the solvent. Predict whether it will be faster or slower in a more polar solvent.

Energy diagram is the graph of energy versus reaction coordinate where the energy and the transition of a chemical reaction is represented. The vertical axis of the energy diagram represents the total potential energy of all the species involved in the reaction. The horizontal axis is called the reaction coordinate. The reaction coordinate symbolizes the progress of the reaction, going from the reactants on the left to the products on the right. The transition state is the highest point on the graph

Step 2:

The structure of the compound and its energy at the transition state determines the rate of a reaction. If we have to speed up the reaction, we have to lower the factors that lowers the energy of the transition state.

Here, the nucleophile is neutral compound. Nucleophiles are usually negatively charged. The reactants starts developing the charge in the transition state and hence it is more charged than the reactants. The polar transition state will be stabilized in a more polar solvent through dipole-dipole interactions, so the rate of reaction will be enhanced in a polar solvent.

Step 3 of 4

Chapter 6, Problem 69SP is Solved
Step 4 of 4

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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