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
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...
icon
Related questions
Question
12
**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.
Expert Solution
steps

Step by step

Solved in 3 steps with 3 images

Blurred answer
Knowledge Booster
Types of Pericyclic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY