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Show how you would convert aniline to the following compound. N=N- OH HO

Show how you would convert aniline to the following compound. N=N- OH HO

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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Title: Conversion of Aniline to a Diazobenzene Compound** **Objective:** Explain the process of converting aniline to the specified compound, through a series of chemical reactions. **Chemical Structure:** The compound shown in the image is a diazobenzene derivative. It contains two benzene rings connected by a diazo group (–N=N–). One of the benzene rings has a hydroxyl group (–OH) in the para position, and the other benzene ring has a hydroxyl group in the ortho position relative to the diazo group. **Step-by-Step Conversion Process:** 1. **Diazotization of Aniline:** - Begin with aniline (C₆H₅NH₂). - Treat aniline with nitrous acid (HNO₂), generated in situ from sodium nitrite (NaNO₂) and hydrochloric acid (HCl), at low temperature (0-5°C) to form the diazonium salt (C₆H₅N₂⁺Cl⁻). 2. **Coupling Reaction:** - The diazonium salt reacts with phenol in an alkaline medium. - The coupling occurs at the ortho and para positions of the phenol due to the activating effect of the hydroxyl group. 3. **Formation of the Target Compound:** - The resultant compound has two benzene rings joined by a –N=N– linkage. - Each benzene ring contains an –OH group, with one in the para position and one in the ortho position relative to the azo linkage, matching the target compound in the image. **Diagram Explanation:** The diagram illustrates the target compound: - Two benzene rings. - A diazo linkage (–N=N–) connecting the rings. - Hydroxyl groups (–OH) attached para on one ring and ortho on the other. This synthesis is a classic example of an azo coupling reaction, commonly used in dye chemistry to create azo dyes. **Conclusion:** The conversion of aniline to the specified diazobenzene compound involves diazotization followed by an azo coupling reaction, providing a practical approach to synthesizing complex aromatic compounds.
Transcribed Image Text:**Title: Conversion of Aniline to a Diazobenzene Compound** **Objective:** Explain the process of converting aniline to the specified compound, through a series of chemical reactions. **Chemical Structure:** The compound shown in the image is a diazobenzene derivative. It contains two benzene rings connected by a diazo group (–N=N–). One of the benzene rings has a hydroxyl group (–OH) in the para position, and the other benzene ring has a hydroxyl group in the ortho position relative to the diazo group. **Step-by-Step Conversion Process:** 1. **Diazotization of Aniline:** - Begin with aniline (C₆H₅NH₂). - Treat aniline with nitrous acid (HNO₂), generated in situ from sodium nitrite (NaNO₂) and hydrochloric acid (HCl), at low temperature (0-5°C) to form the diazonium salt (C₆H₅N₂⁺Cl⁻). 2. **Coupling Reaction:** - The diazonium salt reacts with phenol in an alkaline medium. - The coupling occurs at the ortho and para positions of the phenol due to the activating effect of the hydroxyl group. 3. **Formation of the Target Compound:** - The resultant compound has two benzene rings joined by a –N=N– linkage. - Each benzene ring contains an –OH group, with one in the para position and one in the ortho position relative to the azo linkage, matching the target compound in the image. **Diagram Explanation:** The diagram illustrates the target compound: - Two benzene rings. - A diazo linkage (–N=N–) connecting the rings. - Hydroxyl groups (–OH) attached para on one ring and ortho on the other. This synthesis is a classic example of an azo coupling reaction, commonly used in dye chemistry to create azo dyes. **Conclusion:** The conversion of aniline to the specified diazobenzene compound involves diazotization followed by an azo coupling reaction, providing a practical approach to synthesizing complex aromatic compounds.
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