Oxidation of p-nitrotoluene to p-nitrobenzoic acid
Answers
Answer:
Explanation:
he Nitration Mechanism
(a) Formation of nitronium ion
(i) The sulfuric acid protonates the nitric acid.
(ii) The protonated nitric acid loses a molecule of water to form nitronium ion
(b) Nitration of toluene
(i) Nitronium ion attacks the aromatic ring
Attack occurs at all possible positions to form resonance stabilized carbonation.
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However, the cations formed by ortho and para attack are more stable than those formed by meta attack.
They put the positive charge next to the methyl group, which is electron-donating and adds to the stabilization.
(ii) The hydrogen sulfate ion formed in Step (a) (i) removes a proton from the intermediate, regenerating the aromatic ring and the sulfuric acid catalyst.
II. Synthesis of 4-Nitrobenzoic acid
(a) Friedel-Crafts alkylation of benzene
Benzene to toluen
(b) Nitration of toluene
Toluene to 4-nitrotol
(c). Oxidation of the alkyl side-chain
4-Nitrotoluene to 4-nitrobenzoic acid
III. Synthesis of 3-Nitrobenzoic acid
(a) Friedel-Crafts alkylation of benzene
Benzene to toluene
(b) Oxidation of toluene to benzoic acid
Oxidation
(c) Nitration of benzoic acid
Nitratio