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Question

The increasing order of boiling points of the below mentioned alcohols is
(I) 1,2−dihydroxybenzene
(II) 1,3−dihydroxybenzene
(III) 1,4−dihydroxybenzene
(IV) Hydroxybenzene

A
I<II<IV<III
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B
I<II<III<IV
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C
IV<II<I<III
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D
IV<I<II<III
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Solution

The correct option is D IV<I<II<III
Among the given compounds, hydroxybenzene has least molar mass and hydrogen bonding, therefore possess least boiling point. Among the three isomeric dihydroxybenzenes,
1,2 dihydroxybenzene forms intramolecular H-bonding and so it has lower boiling point than its isomers. On the other hand 1,3dihydroxybenzene and 1,4dihydroxybenzene do not undergo chelation, hence they have extensive intermolecular H-bonding leading to higher boling point. Further intermolecular hydrogen bonding is stronger in the pisomer than the misomer, hence former has highest boiling point. Thus the decreasing order of boiling point is III>II>I>IV
Hence, (d) is the correct option.

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