Carry out the following conversions in not more than 2 steps: (i) Aniline to chlorobenzene (ii) 2-bromopropane to 1- bromopropane?
Aniline
It is one of the simplest and most important aromatic amines, and is used as a starting compound for more complex chemicals. It is mainly used in the manufacture of polyethane urea. As with most volatile amines, aniline has a somewhat unpleasant odor resembling that of rotten fish and an aromatic, burnt taste, and is a particularly pungent poison. It ignites easily, and it burns with a smoky flame.
Hee Carry out the following conversions in not more than 2 steps: (i) Aniline to chlorobenzene (ii) 2-bromopropane to 1- bromopropane?
Synthetic method
Aniline is produced synthetically in two steps, starting with benzene:
- First, the nitration process of benzene is carried out using a concentrated mixture of nitric acid and sulfuric acid at a temperature of 50° to 60° C. This process results in nitrobenzene.
- In the second step, nitrobenzene is hydrogenated, at a temperature (200-300 °C) in the presence of a metal catalyst to give aniline.
The first to reduce nitrobenzene to aniline was Nikolai Zenin in 1842 using inorganic sulfide as a reducing agent (the xenin reaction). The reduction of nitrobenzene to aniline was carried out as part of a reduction reaction carried out by Antoine Beauchamp in 1854 using iron as a reducing agent (Béchamp’s reduction).
As an alternative method, aniline can be prepared from phenol and ammonia, where phenol is derived from cumene.