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DISCUSS THE MECHANISM OF SYNTHESIS OF METHYL ORANGE IN WORDS.

DISCUSS THE MECHANISM OF SYNTHESIS OF METHYL ORANGE IN WORDS.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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DISCUSS THE MECHANISM OF SYNTHESIS OF METHYL ORANGE IN WORDS.

Introduction Methyl orange is an azo dye whose thesis can be accomplished by a diazo coupling reaction between the diazonium salt of sulfanilic acid and N,N-dimethylaniline. Since the coupling reaction is conducted in an acidic solution, the first product to form is the acid form of methyl orange, called helianthin, which is bright red. The addition of a base leads to the conversion of helianthin to its sodium salt, which is methyl orange. H H;C. CH3 OCH3 H3C OAc НОАс H,C ČH3 proton transfer H3C H3C Helianthin (red) NaOH H3C N=N -SO,Na H3C Methyl oran It is necessary to carry out the diazotization reaction in an acidic solution. However, sulfanilic acid is insoluble in acidic solutions. To overcome this problem, the sulfanilic acid is first dissolved in a basic solution: an aqueous solution of sodium carbonate- Sodium nitrite is then added to this basic solution. Finally, the solution is chilled and then acidified with hydrochloric acid. The instant the sulfanilic acid precipitates from the solution, it becomes diazotized, yielding a finely divided white precipitate of the diazonium salt of sulfanilic acid. This diazonium salt is allowed to react immediately with dimethylaniline in the solution in which it was precipitated.
Transcribed Image Text:Introduction Methyl orange is an azo dye whose thesis can be accomplished by a diazo coupling reaction between the diazonium salt of sulfanilic acid and N,N-dimethylaniline. Since the coupling reaction is conducted in an acidic solution, the first product to form is the acid form of methyl orange, called helianthin, which is bright red. The addition of a base leads to the conversion of helianthin to its sodium salt, which is methyl orange. H H;C. CH3 OCH3 H3C OAc НОАс H,C ČH3 proton transfer H3C H3C Helianthin (red) NaOH H3C N=N -SO,Na H3C Methyl oran It is necessary to carry out the diazotization reaction in an acidic solution. However, sulfanilic acid is insoluble in acidic solutions. To overcome this problem, the sulfanilic acid is first dissolved in a basic solution: an aqueous solution of sodium carbonate- Sodium nitrite is then added to this basic solution. Finally, the solution is chilled and then acidified with hydrochloric acid. The instant the sulfanilic acid precipitates from the solution, it becomes diazotized, yielding a finely divided white precipitate of the diazonium salt of sulfanilic acid. This diazonium salt is allowed to react immediately with dimethylaniline in the solution in which it was precipitated.
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