Question

An organic compound (X) with molecular formula `C_(7)H_(8)O` is insoluble in aqueous `NaHCO_(3)` but dissolves in NaOH. When treated with bromine water (X) rapidly gives (Y), `C_(7)H_(5)Obr_(3)`. The compounds (X) and (Y) respectively are
A. Benzyl alcohol and 2,4,6-tribromo-3-methoxy benzene
B. Benzyl alcohol and 2,4,6-tribromo-3-methyl phenol
C. o-cresol and 3,4,6-tribromo-2-methyl phenol
D. m-cresol and 2,4,6-tribromo-3-methyl phenol

Answer 1

Compound (X) must be a phenolic compound as shown by various reactions. (X) on treatment with `Br_(2)` water gives (Y) with 3Br atoms, so the placement of OH and `CH_(3)` must be such that they reinforce each other in electrophilic substitution . So, the compound (X) is m-cresol and (Y) is 2,4,6-tribromo-3 methyl phenol.