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Factors Affecting Hydrogen Bonding

Account for t...

Question

Account for the following:
Carboxylic acids with five or fewer carbon atoms are water soluble but, higher ones are insoluble.

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Solution

The solubility of $R C O O H$ in water is due to hydrogen bonding of $- C O O H$ group and water. R-portion being lycophobic resists solubility. As $R$ gets large, this factor prevails over the first factor and thus, higher acids become insoluble

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Factors Affecting Hydrogen Bonding

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