Problems and exercisesPreparation
1. Why not like an alcohol?
Explain why phenol cannot be obtained by heating bromobenzene with aqueous NaOH at 100 °C, whereas 1-bromobutane gives 1-butanol under those conditions.
2. The cumene process
Write the three stages of the cumene process and state which by-product is obtained and why it matters.
3. From an amine
How would you prepare 4-methylphenol (p-cresol) from 4-methylaniline (p-toluidine)?
4. Synthesis from benzene
Propose a synthesis of 3-bromophenol from benzene. Hint: OH directs ortho and para; choose a meta-directing group that can later be converted into OH.
5. Which reacts most easily?
Order by ease of hydrolysis with aqueous NaOH: chlorobenzene, 1-chloro-4-nitrobenzene and 1-chloro-2,4-dinitrobenzene.