I am doing my Advanced Higher Investigation and it is on Preparation of Paracetamol. I have to explain the chemistry behind the three stages - nitration of phenol; reduction of a nitro group to amine; formation of an amide.
We're only on unit two right now, and I have read the unit three organic chem notes and they make no sense.
Thanks so much in advance!
AH Chemistry help! Watch
- Thread Starter
- 08-12-2010 19:08
- 08-12-2010 19:45
the nitration is an electrophilic substitution on phenol by the NO2+ (from nitric acid) ion. It forms a carbocation intermediate (wheland intermediate) before eliminating the hydrogen. You'll get a mixture of products by substitution on the ortho- and para- sites of the phenol (OH is an a/p directing group)
the reduction can occur by a number of methods, there are lots of reagents for this one. Tin Chloride and HCl is one method.
Amide formation is normally using an acyl chloride, which would be a nucleophilic substitution by the amine.
Do you need to have mechanisms? What information do you need to know or not understand from the notes?Last edited by gingerbreadman85; 08-12-2010 at 19:47.