what us electropbilic substitution ?
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In order to elucidate the mechanism of anodic acetoxylation, a number of organic compounds, most of them aromatic, have been studied polarographically at a rotating platinum anode in acetic acid-0.5 M sodium acetate solution. Half-wave potentials thus obtained demonstrate that the organic substrate participates in an electrochemical process which takes place at a potential considerably lower than the discharge potential of the acetate ion. Controlled potential electrolysis of naphthalene, biphenyl, anisole, phenyl acetate, mesitylene, durene, and hexamethylbenzene confirms that acetates are formed at low anode potentials. For the polymethylbenzenes side-chain acetoxylation is observed, mesitylene being a borderline case. 1,1-Diphenylethylene and N,N-dimethylformamide, which previously have been shown to give acetoxylation products on electrolysis in acetic acid-sodium acetate, give the same products on controlled potential electrolysis. A mechanism involving an initial two-electron transfer from the organic substrate to the anode to form a dicationic intermediate, followed by reaction with acetate ion and loss of a proton, is proposed for anodic oxidation of aromatic compounds. The side-chain substitution products can be accounted for by assuming that the intermediate loses a proton from one methyl group to form a benzyl cation. A number of other anodic substitution processes probably conform to a similar mechanism.
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In order to elucidate the mechanism of anodic acetoxylation, a number of organic compounds, most of them aromatic, have been studied polarographically at a rotating platinum anode in acetic acid-0.5 M sodium acetate solution. Half-wave potentials thus obtained demonstrate that the organic substrate participates in an electrochemical process which takes place at a potential considerably lower than the discharge potential of the acetate ion. Controlled potential electrolysis of naphthalene, biphenyl, anisole, phenyl acetate, mesitylene, durene, and hexamethylbenzene confirms that acetates are formed at low anode potentials. For the polymethylbenzenes side-chain acetoxylation is observed, mesitylene being a borderline case. 1,1-Diphenylethylene and N,N-dimethylformamide, which previously have been shown to give acetoxylation products on electrolysis in acetic acid-sodium acetate, give the same products on controlled potential electrolysis. A mechanism involving an initial two-electron transfer from the organic substrate to the anode to form a dicationic intermediate, followed by reaction with acetate ion and loss of a proton, is proposed for anodic oxidation of aromatic compounds. The side-chain substitution products can be accounted for by assuming that the intermediate loses a proton from one methyl group to form a benzyl cation. A number of other anodic substitution processes probably conform to a similar mechanism.
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