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Can someone Outline a chemical reaction for the formation of the compound and explain it and detail I really need to understand what is going on in the mechanism

Can someone Outline a chemical reaction for the formation of the compound and explain it and detail I really need to understand what is going on in the mechanism

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 8CTQ
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Can someone Outline a chemical reaction for the formation of the compound and explain it and detail I really need to understand what is going on in the mechanism 

Introduction Oxidations are a very important class of reactions in organic chemistry. Most oxidations require either a heteroatom in a reduced state (oxygen in -OH, nitrogen in –NH2, etc.) or a carbon-carbon T-bond (ozonolysis of alkenes and alkynes (and peroxide), the formation of oxiranes from alkenes using peroxy acids, etc.). The oxidation of an aromatic side chain does not require any of these factors. All that is needed is a benzylic carbon with at least one hydrogen attached to it. The oxidizing agents that can be used are chromic acid (using Na2Cr2O7 or CrO3 in sulfuric acid and water) or potassium permanganate (KMNO4). The product in each case is benzoic acid or a derivative of benzoic acid (the permanganate reaction requires to work up with acid because the permanganate reaction generates a basic solution as a byproduct): CH3 СООН 1. КMnOд, Н,О, д 2. Н,О", Н,О CH3 COOH CrO3, H,SO4, H,O H2O, heat NO2 NO2 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. KMnOд, H,О, д 2. HСІ, 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:Introduction Oxidations are a very important class of reactions in organic chemistry. Most oxidations require either a heteroatom in a reduced state (oxygen in -OH, nitrogen in –NH2, etc.) or a carbon-carbon T-bond (ozonolysis of alkenes and alkynes (and peroxide), the formation of oxiranes from alkenes using peroxy acids, etc.). The oxidation of an aromatic side chain does not require any of these factors. All that is needed is a benzylic carbon with at least one hydrogen attached to it. The oxidizing agents that can be used are chromic acid (using Na2Cr2O7 or CrO3 in sulfuric acid and water) or potassium permanganate (KMNO4). The product in each case is benzoic acid or a derivative of benzoic acid (the permanganate reaction requires to work up with acid because the permanganate reaction generates a basic solution as a byproduct): CH3 СООН 1. КMnOд, Н,О, д 2. Н,О", Н,О CH3 COOH CrO3, H,SO4, H,O H2O, heat NO2 NO2 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. KMnOд, H,О, д 2. HСІ, 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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