1.)Please explain an overview of the reaction sequence. 2.) discuss each type of
ID: 517016 • Letter: 1
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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