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Chemistry

9th Edition
Steven S. Zumdahl
ISBN: 9781133611097

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BuyFindarrow_forward

Chemistry

9th Edition
Steven S. Zumdahl
ISBN: 9781133611097
Textbook Problem

Is octanoic acid more soluble in 1 M HCl, 1 M NaOH, or pure water? Explain. Drugs such as morphine (C17H19NO3) are often treated with strong acids. The most commonly used form of morphine is morphine hydrochloride (C17H20ClNO3). Why is morphine treated in this way? (Hint: Morphine is an amine.)

Interpretation Introduction

Interpretation: The extent of solubility of octanoic acid in 1MHCl,1MNaOH , or pure water is to be explained and the treatment of morphine with strong acids is to be stated.

Concept introduction: Octanoic acid (C8H16O2) is a carboxylic acid. Carboxylic acids undergo nucleophilic addition reactions as it contains -OH nucleophile and formed derivatives of acid. As carboxylic acids are weak acids they partially dissociate to form H+ and RCOO- ions. Amines react with hydrochloric acid to form soluble compounds.

To determine: The extent of solubility of octanoic acid in 1MHCl,1MNaOH , or pure water and the treatment of morphine with strong acids.

Explanation

Explanation

Octanoic acid is more soluble in 1MNaOH than the remaining two solvents.

The reaction of octanoic acid with 1MNaOH is,

Figure 1

Octanoic acid on reaction with water, slightly ionizes to give moderately acidic solution. The solubility of octanoic acid in hydrochloric acid is reduced because of common ion effect as both are acidic in nature and contain common ions.

When octanoic acid reacts with 1MNaOH , water soluble carboxylate ion is formed

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