1.)Please explain an overview of the reaction sequence. 2.) discuss each type of

Question

1.)Please explain an overview of the reaction sequence. 2.) discuss each type of reaction (acetylation, oxidation, hydrolysis)

Synthesis of PABA 16 PABA, p-aminobenzoic acid, is used commercially as sunscreen. In this experiment, you will synthesize p-aminobenzoic acid in a three-step sequence starting with p-toluidine. In the first step p toluidine is protected against oxidation by acetylation with acetic anhydride. In the second step, the methyl group is oxidized with potassium permanganate to p-acetoamidobenzoic acid. Hydrolysis of the acetamido group regenerates the amine as p-aminobenzoic acid NH2 CH HN HN H20, H. KMno4 HCI O' Na CHa PABA. p-methylacetanilide p-acetami dobenzoic acid p-Toluidine mp 188 °C mp 250-252 °C mp 149 151 oC MW 107 MW 137 MW 179 MW 149 Pre-Lab Questions

Explanation / Answer

1) The reaction sequence indicates that initailly -NH2 group has been blocked and further the -CH3 group is oxidized to -COOH by using oxidizing agent.

2) In acetylation process, -NH2 group is acetylated by acetic anhydride, this reaction is followed by oxidation with strong oxidizing agent. This will be concluded by using hydrolysis to get back -NH2 group its original state.

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