- Aniline, NaNO2 + HCl, H2O, heating
- Cumene, O2, H3O+


The structure of phenol is as follows:


1. When aniline reacts with NaNO2/HCl then diazonium salt is formed. When diazonium salt reacts with water then phenol is obtained as a product.


2. Cumene (isopropylbenzene) is oxidized in the presence of air to cumene hydroperoxide. It is converted to phenol and acetone by treating it with dilute acid. Acetone, a by-product of this reaction, is also obtained in large quantities by this method. The reaction is as follows:


3. Chlorobenzene does not react with NaOH at STP condition. It reacts with NaOH at high pressure and temperature. Thus, in the third reaction phenol is not obtained as a product.
4. Benzene is sulphonated with oleum and benzene sulphonic acid so formed is converted to sodium phenoxide on heating with molten sodium hydroxide. Acidification of the sodium salt gives phenol. The reaction is as follows:


Hence, option third is the correct answer.









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