Which one of the following reaction sequence is incorrect method to prepare phenol?
- [figure] , oleum, NaOH, H3O+
- Aniline, NaNO2 + HCl, H2O, heating
- Cumene, O2, H3O+
- [figure] , NaOH, STP condition
Answer
(4) [figure] , NaOH, STP condition
Solution
(1) Benzene oleum benzenesulphonic acid NaOH sodium phenoxide H3O+ phenol — correct.
(2) Aniline NaNO2 + HCl benzenediazonium chloride H2O, warm phenol — correct.
(3) Cumene O2 cumene hydroperoxide H3O+ phenol + acetone — correct.
(4) As per NCERT, chlorobenzene gives sodium phenoxide with NaOH only at 623 K and 300 atm, because the C–Cl bond has partial double bond character. At STP no reaction occurs.
∴ Method (4) is incorrect.
Answer: (4)