Question

* Which of the proposed reaction sequence is best to carry out each of the following conversion? Assume ortho and para isomers can be separated. CO2H 0-0 NH2 a. 1. CH3C1, AIC13 2. HNO3, H2SO4 3. KMnO4, H30+ 4. Hz/Ni 1. CH3C1, A1C13 2. KMnO4, H30 3. HNO3, H2SO4 4. H2/Ni 1. HNO3, H2SO4 2. H2Ni 3. CH3C1, A1C13 4. KMnO4, H30 1. HNO3, H2SO4 2. CH3C1, A1C13 3. Hz/Ni 4. KMnO4, H30

Answer 1

Conversion of benzene to 4-aminobenzoic acid

COOH benzene NH2 4-aminobenzoic acid

1. 1st step should be alkylation of benzene using friedel craft alkylation
2. 2nd step is nitration of benzene. Since alkyl group is ortho para directing. Directs nitro group to substitute at the para position.
3. Oxidation of alkyl group using a strong oxidising agent.
4. reduction of nitro group using a mild reducing agent

OH CH3C1 KMnO4 conc.HNO3 ОН- anhyd AlCl3 H2SO4 NO2 NOZ COOH H2/Ni

option A

1. CH3Cl/anhyd.AlCl3

2.HNO3/H2SO4

3.KMnO4/H3O+

4.H2/Ni