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12) What is reagent A, which is necessary to complete the following conversion? O Br NH₂ Br NaNO₂/HCI A < 5°C CI Br Br

12) What is reagent A, which is necessary to complete the following conversion? O Br NH₂ Br NaNO₂/HCI A < 5°C CI Br Br

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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**Question 12:** What is reagent A, which is necessary to complete the following conversion? **Chemical Conversion Details:** - **Reactant Structure:** The starting compound is a benzene ring with three substituents: a bromine (Br) atom, an amino group (NH₂), and a chlorine (Cl) atom, arranged with the bromine and amino groups ortho to each other. - **Reaction Conditions:** The reactant is treated with sodium nitrite (NaNO₂) and hydrochloric acid (HCl) at a temperature below 5°C. - **Intermediate Reaction Step:** The reaction results in the formation of a diazonium salt intermediate, not shown, which requires further treatment with reagent A. - **Product Structure:** The product structure is a benzene ring with bromine and chlorine atoms in the same positions as the original reactant, but the amino group is removed. **Explanation of Conversion Process:** 1. **Formation of Diazonium Salt:** The initial step involves treating the amino-substituted benzene with NaNO₂ and HCl to form a diazonium ion intermediate. 2. **Role of Reagent A:** Reagent A is typically a reducing agent or a nucleophile that completes the conversion process by replacing the diazonium group. 3. **Final Product:** The final aromatic compound retains the original bromine and chlorine substituents, while the position formerly occupied by the amino group is now a hydrogen atom. In this reaction, reagent A is likely hypophosphorous acid (H₃PO₂), which facilitates the conversion of the diazonium salt to the plain benzene ring by reducing the diazonium group.
Transcribed Image Text:**Question 12:** What is reagent A, which is necessary to complete the following conversion? **Chemical Conversion Details:** - **Reactant Structure:** The starting compound is a benzene ring with three substituents: a bromine (Br) atom, an amino group (NH₂), and a chlorine (Cl) atom, arranged with the bromine and amino groups ortho to each other. - **Reaction Conditions:** The reactant is treated with sodium nitrite (NaNO₂) and hydrochloric acid (HCl) at a temperature below 5°C. - **Intermediate Reaction Step:** The reaction results in the formation of a diazonium salt intermediate, not shown, which requires further treatment with reagent A. - **Product Structure:** The product structure is a benzene ring with bromine and chlorine atoms in the same positions as the original reactant, but the amino group is removed. **Explanation of Conversion Process:** 1. **Formation of Diazonium Salt:** The initial step involves treating the amino-substituted benzene with NaNO₂ and HCl to form a diazonium ion intermediate. 2. **Role of Reagent A:** Reagent A is typically a reducing agent or a nucleophile that completes the conversion process by replacing the diazonium group. 3. **Final Product:** The final aromatic compound retains the original bromine and chlorine substituents, while the position formerly occupied by the amino group is now a hydrogen atom. In this reaction, reagent A is likely hypophosphorous acid (H₃PO₂), which facilitates the conversion of the diazonium salt to the plain benzene ring by reducing the diazonium group.
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