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Question

(I) 1,2-dihydroxybenzene
(II) 1,3-dihydroxybenzene
(III) 1,4-dihydroxybenzene
(IV) Hydroxybenzene.
The increasing order of boiling points of above mentioned alcohols is:

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

The correct option is C IV < I < II < III
1, 4-dihydroxybenzene has intermolecular hydrogen bonding. So, it has the highest boiling point among all the given compounds.
1, 2-dihydroxybenzene has intramolecular hydrogen bonding. So, the boiling point will be less than that of 1, 4-dihydroxybenzene.
1, 3-dihydroxybenzene shows partial intermolecular and intramolecular hydrogen bonding. So, it has more boiling point than 1, 2-dihydroxybenzene and less than 1, 2-dihydroxybenzene. Hydroxybenzene does not have any hydrogen bonding, so it's boiling point is least among the three.
So the correct order is: (III)>(II)>(I)>(IV)

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