Question

Rank the following acids below from least soluble to most soluble in water. Which acid listed...

Rank the following acids below from least soluble to most soluble in water. Which acid listed below is the most soluble in water?

Acid

Name

Molecular

Weight

Melting

Point

Cinnamic Acid

148.16

132-33

4-Hydroxyphenylacetic Acid

152.15

148-150

p-Anisic Acid

152.15

183

Hippuric Acid

179.17

188-190

Azelaic Acid

188.22

110

Sebacic Acid

202.25

135

Homework Answers

Answer #1

A carboxylic acid with lower molecular weight will form more number of hydrogen bonds with water. Thus it will be more soluble in water.

So among the given acids the increasing order of their solubilities are:

Sebacic acid> Azelaic acid>Hippuric acid> p ansic acid> 4-hydroxyphenyl acetic acid> Cinnamic acid

Among Hippuric acid and 4-hydroxylpehnyl acetic acid, 4-hydroxyphenyl acetic acid has 2 -OH group’s so it will have strong hydrogen bonding than in Hippuric acid.

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