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Methyl Orange Synthesis Lab Report

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Experiment 11B consisted of synthesizing methyl orange, a synthetic dye, and testing this dye’s coloring quality and effectiveness as a pH indicator. Methyl orange is an acid-base indicator. In a pH of greater than 4.4, it becomes a yellow solution with a negatively charged sulfonate ion. When submerged into a solution with a pH less than 3.2, the dipolar red ion (helianthin) predominates. Methyl orange is a type of azo dye, which is commonly found in food, fabric, paint, and other brightly colored products. The general structure consists of the N5N functional group sandwiched between two aromatic species. Azo dyes are brightly colored because of their extensive conjugated system which gives rise to a strong chromophore. The exact color depends on both the nature of the aromatic group and the substituents. Methyl orange is synthesized through an azo coupling reaction between a diazonium ion and N,N-dimethylaniline. An electrophilic aromatic substitution causes the positively charged diazonium ion to act as the electrophilic species. In the first step of azo coupling the diazonium intermediate is synthesized. This process is called diazonation, in which the diazonium intermediate is formed by the reaction between sulfanilic acid (an aromatic amine) …show more content…

After this we added .5g of NaCl and allowed the solution to cool to room temperature then placed it into an ice bath. The reaction mixture turned into a lighter shade of yellow and began to crystallize. The crystals were filtered through a Buchner funnel and rinsed twice with saturated aqueous NaCl solution. The reaction mixture was placed in a boiling water bath in order to dissolve most of the dye and all the contaminating salts. It was then cooled in a ice bath and filtered using a Buchner funnel. The product obtained was shiny and a metallic gray-gold color. The product weighed in at .207g of methyl orange, giving us a percent yield of

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