Which of the following compounds would you expect to be most soluble in water?

C_{2} H_{5} - O - C_{2} H_{5}

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C H_{3} - C O_{2} H

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C_{6} H_{5} - N H_{2}

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C_{6} H_{5} - C O O C_{2} H_{5}

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Solution

The correct option is A $C H_{3} - C O_{2} H$
$C H_{3} C O O H$ is a carboxylic acid. It forms most extensive intermolecular hydrogen bonds with water. Hence, it is most soluble in water.
The degree of hydrogen bonding in aniline is less than that in acetic acid. Also it has a bulky hydrophobic phenyl group. Hence, it is less soluble than acetic acid.
Diethyl ether and ethyl benzoate do not form hydrogen bonds with water. Hence, they have the least solubility.

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