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hat kind of reaction is the reaction between N, N-diethylaniline, and diazonium salt? Supply a mechanism for this coupling reaction.

hat kind of reaction is the reaction between N, N-diethylaniline, and diazonium salt? Supply a mechanism for this coupling reaction.

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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1. What kind of reaction is the reaction between N, N-diethylaniline, and diazonium salt? Supply a mechanism for this coupling reaction.  

## Introduction Methyl orange is an azo dye synthesized through a diazo coupling reaction between the diazonium salt of sulfanilic acid and *N,N*-dimethylaniline. Initially, the reaction occurs in an acidic solution, leading to the formation of an acid form of methyl orange, known as heliantin, which is bright red. The subsequent addition of a base transforms heliantin into its sodium salt, methyl orange. ### Reaction Steps and Diagrams 1. **Formation of Diazonium Salt:** Begin with a diazonium salt reaction between sulfanilic acid and sodium nitrite under acidic conditions. 2. **Initial Acid Formation:** The initial product is heliantin, depicted in the diagram as a protonated molecule in bright red. 3. **Base Addition and Transformation:** The addition of a base (NaOH in the diagram) causes a proton transfer, resulting in methyl orange formation, depicted in its sodium salt form. ### Detailed Description The synthesis involves a diazo coupling reaction requiring an acidic solution, although sulfanilic acid is typically insoluble in such mediums. To address this, sulfanilic acid is dissolved in a basic solution (aqueous sodium carbonate). Sodium nitrite is then introduced to this basic medium. The solution is subsequently chilled and acidified using hydrochloric acid. Sulfanilic acid precipitates as a diazonium salt, finely divided and ready to react with dimethylaniline. Upon reaction and further processing, methyl orange is ultimately formed. **Key Points in Diagrams:** - **Structures:** Molecular structures are illustrated, demonstrating the transition from reactants to intermediates and final products. - **Reversible Arrows:** Indicate equilibrium and reaction conditions, such as acidic to basic shifts. - **Color Indication:** Heliantin is shown in a protonated red form, differentiating from the final yellow-orange product, methyl orange. Understanding the mechanism and steps involved in the synthesis of methyl orange provides insights into azo dye production's chemical processes.
Transcribed Image Text:## Introduction Methyl orange is an azo dye synthesized through a diazo coupling reaction between the diazonium salt of sulfanilic acid and *N,N*-dimethylaniline. Initially, the reaction occurs in an acidic solution, leading to the formation of an acid form of methyl orange, known as heliantin, which is bright red. The subsequent addition of a base transforms heliantin into its sodium salt, methyl orange. ### Reaction Steps and Diagrams 1. **Formation of Diazonium Salt:** Begin with a diazonium salt reaction between sulfanilic acid and sodium nitrite under acidic conditions. 2. **Initial Acid Formation:** The initial product is heliantin, depicted in the diagram as a protonated molecule in bright red. 3. **Base Addition and Transformation:** The addition of a base (NaOH in the diagram) causes a proton transfer, resulting in methyl orange formation, depicted in its sodium salt form. ### Detailed Description The synthesis involves a diazo coupling reaction requiring an acidic solution, although sulfanilic acid is typically insoluble in such mediums. To address this, sulfanilic acid is dissolved in a basic solution (aqueous sodium carbonate). Sodium nitrite is then introduced to this basic medium. The solution is subsequently chilled and acidified using hydrochloric acid. Sulfanilic acid precipitates as a diazonium salt, finely divided and ready to react with dimethylaniline. Upon reaction and further processing, methyl orange is ultimately formed. **Key Points in Diagrams:** - **Structures:** Molecular structures are illustrated, demonstrating the transition from reactants to intermediates and final products. - **Reversible Arrows:** Indicate equilibrium and reaction conditions, such as acidic to basic shifts. - **Color Indication:** Heliantin is shown in a protonated red form, differentiating from the final yellow-orange product, methyl orange. Understanding the mechanism and steps involved in the synthesis of methyl orange provides insights into azo dye production's chemical processes.
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