1.In retro synthesis: How do we know the bond between Carbon and NO2 will break first?? Why does not Br bond break first? 2. Is it matter that which bond break first ?

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
icon
Concept explainers
Question

1.In retro synthesis: How do we know the bond between Carbon and NO2 will break first?? Why does not Br bond break first?

2. Is it matter that which bond break first ? 

3. When it asked "what immediate the precusrsor" , what specificly does it means??? why it's important?

4. What steps or rule should we follow when solving retrosynthesis questions?

**Chapter 16: Synthesis of Polysubstituted Benzenes**

**A. Retro-synthesis:**

1. Structure: A benzene ring with a bromine (Br) and nitro group (NO₂). 

   - **Activator**: CH₃ (methyl group), an ortho-, para-director.
   - **Deactivator**: NO₂, a meta-director.

2. Question: "What is an immediate precursor?"
   
   - A benzene with CH₃ and Br groups.
   - Reaction arrow towards a benzene with only a CH₃ group.
   - Question: "What's the immediate precursor?"

**Synthesis Process:**

1. Starting from benzene:
   1. Add CH₃Cl in presence of AlCl₃ to attach a CH₃ group.
   2. Add Br₂ with FeBr₃ to introduce Br.
   3. Add HNO₃ with H₂SO₄ for nitration, leading to a benzene with CH₃, Br, and NO₂.

   - Note: CH₃ dominates (refer to graph, slide 18).
   - Ortho-product separation is possible.

**B. Retro-synthesis:**

1. Structure: Benzene with CH₃, Br, and NO₂ groups.
   
   - Reaction arrow points towards a benzene ring first with Br, then with just a CH₃ group.

**Synthesis Process:**

1. Starting from benzene:
   1. Add Br₂ with FeBr₃ to form bromobenzene.
   2. Add CH₃Cl in presence of AlCl₃ for methylation.
   3. Finally, add HNO₃ with H₂SO₄ for nitration, resulting in the final product.

Diagrams show the step-by-step progression in both the synthesis and retro-synthesis processes of polysubstituted benzenes.
Transcribed Image Text:**Chapter 16: Synthesis of Polysubstituted Benzenes** **A. Retro-synthesis:** 1. Structure: A benzene ring with a bromine (Br) and nitro group (NO₂). - **Activator**: CH₃ (methyl group), an ortho-, para-director. - **Deactivator**: NO₂, a meta-director. 2. Question: "What is an immediate precursor?" - A benzene with CH₃ and Br groups. - Reaction arrow towards a benzene with only a CH₃ group. - Question: "What's the immediate precursor?" **Synthesis Process:** 1. Starting from benzene: 1. Add CH₃Cl in presence of AlCl₃ to attach a CH₃ group. 2. Add Br₂ with FeBr₃ to introduce Br. 3. Add HNO₃ with H₂SO₄ for nitration, leading to a benzene with CH₃, Br, and NO₂. - Note: CH₃ dominates (refer to graph, slide 18). - Ortho-product separation is possible. **B. Retro-synthesis:** 1. Structure: Benzene with CH₃, Br, and NO₂ groups. - Reaction arrow points towards a benzene ring first with Br, then with just a CH₃ group. **Synthesis Process:** 1. Starting from benzene: 1. Add Br₂ with FeBr₃ to form bromobenzene. 2. Add CH₃Cl in presence of AlCl₃ for methylation. 3. Finally, add HNO₃ with H₂SO₄ for nitration, resulting in the final product. Diagrams show the step-by-step progression in both the synthesis and retro-synthesis processes of polysubstituted benzenes.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Basics in Organic Reaction Mechanisms
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