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Question
The melting points and solubility in water of amino acids are generally higher than that of the corresponding halo acids. Explain.
Solution 1
Both acidic (carboxyl) as well as basic (amino) groups are present in the same molecule of amino acids. In aqueous solutions, the carboxyl group can lose a proton and the amino group can accept a proton, thus giving rise to a dipolar ion known as a zwitter ion.
Due to this dipolar behaviour, they have strong electrostatic interactions within them and with water. But halo-acids do not exhibit such dipolar behaviour.
For this reason, the melting points and the solubility of amino acids in water is higher than those of the corresponding halo-acids.
Solution 2
The amino acids exist as zwitter ions, H3N+ — CHR-COO-. Due to this dipolar salt like character, they have strong dipole-dipole attractions. Therefore, their melting points are higher than corresponding haloacids which do not have salt like character.
Due to salt like character, amino acids intereact strongly with water. As a result, their solubility in water is higher than corresponding haloacids which do not have salt like character.
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