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 |
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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