Aromatic Side-Chain Oxidation: o-Chlorobenzoic Acid from o-Chlorotoluene Q) Supply a correctly balanced equation for this reaction (Hint: It is easiest to determine the oxidation state of the methyl carbon of the toluene, and the carbonyl carbon of the acid. Also, determine the oxidation states for the manganese in both the permanganate ion and the MnO2. Balance the equation based on the correct number of electrons gained, and lost.)

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Aromatic Side-Chain Oxidation: o-Chlorobenzoic Acid from o-Chlorotoluene

Q) Supply a correctly balanced equation for this reaction (Hint: It is easiest to determine the oxidation state of the methyl carbon of the toluene, and the carbonyl carbon of the acid. Also, determine the oxidation states for the manganese in both the permanganate ion and the MnO2. Balance the equation based on the correct number of electrons gained, and lost.)

 

In the experiment, potassium permanganate is used to oxidize 2-chlorotoluene (o-chlorotoluene)
to 2-chlorobenzoic acid (o-chlorobenzoic acid). Permanganate solutions are less hazardous than
those containing chromium compounds, which are often carcinogenic.
CH3
СООН
1. КMnO4, H,0, д
2. HCІ, Н-О
Cl
Cl
The yield of the reaction observed in the literature (Clarke, H. T.; Taylor, E. R. Org. Synth. 1930,
10, 20) is 76-78 % before recrystallization and 65-67 % after recrystallization.
Transcribed Image Text:In the experiment, potassium permanganate is used to oxidize 2-chlorotoluene (o-chlorotoluene) to 2-chlorobenzoic acid (o-chlorobenzoic acid). Permanganate solutions are less hazardous than those containing chromium compounds, which are often carcinogenic. CH3 СООН 1. КMnO4, H,0, д 2. HCІ, Н-О Cl Cl The yield of the reaction observed in the literature (Clarke, H. T.; Taylor, E. R. Org. Synth. 1930, 10, 20) is 76-78 % before recrystallization and 65-67 % after recrystallization.
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