Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 14, Problem 14.17P
Interpretation Introduction

(a)

Interpretation:

The equilibrium constant for the reaction of alkyne with sodium amide in liquid ammonia is to be stated. Also, the equilibrium constant for the reaction of alkane with amide ion is to be stated.

Concept introduction:

Acetylenic anions are formed when an alkene is reacted with a stronger base like sodium amide in liquid ammonia. Amide is a stronger base than acetylenic ion, therefore, it easily removes a proton from alkynes and the reaction is favored in the forward direction. Equilibrium reaction is the reaction in which the rate of forward direction is equal to the rate of reverse reaction. Equilibrium constant is a constant at any point of equilibrium; where, the ratio of the concentration of the products, each raised to power of their respective coefficient, to the concentration of the reactants, each raised to a power of their respective coefficient. Equilibrium constant depends only on temperature.

Interpretation Introduction

(b)

Interpretation:

The reason as to why sodium amide cannot be used to form alkyl anions from alkanes is to be stated.

Concept introduction:

Acetylenic anions are formed when an alkene is reacted with a stronger base like sodium amide in liquid ammonia. Amide is a stronger base than acetylenic ion, therefore, it easily removes a proton from alkynes and the reaction is favored in the forward direction. Equilibrium reaction is the reaction in which the rate of forward direction is equal to the rate of reverse reaction. Equilibrium constant is a constant at any point of equilibrium; where, the ratio of the concentration of the products, each raised to power of their respective coefficient, to the concentration of the reactants, each raised to a power of their respective coefficient. Equilibrium constant depends only on temperature.

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