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Question

Structure of molecules of two compounds are given below :
(a) Which of the two compounds will have inter molecular hydrogen bonding and which compound is expected to show intramolecular hydrogen bonding.
(b) The melting point of a compound depends on, among other things, the extent of hydrogen bonding. On this basis explain which of the above two compounds will show higher melting point.
(c) Solubility of compounds in water depends on power to form hydrogen bonds with water. Which of the above compounds will form hydrogen bond with water easily and be more soluble in it?

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Solution

(a) Compound (i) will form an intramolecular hydrogen bond because NO2 and OH group are close together in comparison to that in compound (II).

(b) Compound (II) will have a higher melting point because it forms intermolecular hydrogen bonds. Thus, more and more molecules are joined together through hydrogen bond formation.

(c) Due to the intramolecular hydrogen bonding compound (I) will not be able to form hydrogen bonds with water thus will be less soluble in it while compound (II) can form will be soluble in water due to intermolecular hydrogen bonding with water.

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