question_answer

An organic compound X with molecular formula,\[{{C}_{7}}{{H}_{8}}O\]is insoluble in aqueous \[NaHC{{O}_{3}}\]but dissolves in NaOH. When treated with bromine water X rapidly gives\[Y,{{C}_{7}}{{H}_{5}}OB{{r}_{3}}\]. The compounds X and V 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, 5-tribromo-2-methyl phenol

D) methoxybenzene and 2, 4, 6-tribromo-3- methoxy benzene

E)  m-cresol and 2, 4, 6-tribromo-3-methyl phenol

Correct Answer: E

Solution :

Compound X\[({{C}_{7}}{{H}_{8}}O)\]insoluble in aqueous \[NaHC{{O}_{3}}\]but soluble in\[NaOH,\]so it is a phenol. Since the number of carbon atoms remains the same after bromination, the compound must be meta cresol and reactions takes place as follows: