JEE Main Chemistry question

[IIT 2006] The increasing order of boiling points of (I) benzene-1,2-diol (catechol), (II) benzene-1,3-diol (resorcinol), (III) benzene-1,4-diol (hydroquinone) and (IV) phenol is

(A)I < II < III < IV
(B)I < II < IV < III
(C)IV < I < II < IIICorrect
(D)IV < II < I < III

Answer: (C)

Solution

Phenol, with only one –OH, has the least intermolecular hydrogen-bonding capacity and the lowest boiling point of the four. Among the diols, catechol's adjacent –OH groups partly satisfy their H-bonding ability *intramolecularly*, reducing

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Question ID VK-140104