Please provide a plausible synthesis for the following overall transformation. Please include all necessary workup steps. For each step, please include both the reagents required and also please draw each intermediate structure. H OMe LOMM PhMg Br 2) H30* CH3OH O-H Na:O-H AlCl3 Nao CH3-CHa Naßr: CI-Al-cr

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

Hello Can somone check my mechanism, i was told on the last step to use an acid but if ithink the CH3OH would give me the dimethyl with oxygen.  

**Title: Synthesis Pathway for Chemical Transformation**

---

**Objective:**
Provide a plausible synthesis for the given overall chemical transformation. Include all necessary workup steps, reagents, and draw each intermediate structure.

**Transformation Overview:**
The transformation begins with an aldehyde and converts it into a methoxy substituted aromatic compound with an extended carbon chain.

**Step-by-Step Synthesis:**

1. **Grignard Addition:**
   - **Reagents:** 1) PhMgBr (phenylmagnesium bromide), 2) H₃O⁺
   - **Intermediate Structure:** After Grignard addition, the resulting intermediate is a secondary alcohol with a phenyl group.

2. **Alkoxide Formation:**
   - **Reagents:** Na⁺ O⁻ H (sodium hydroxide)
   - **Process:** The hydroxyl group is deprotonated to form an alkoxide ion.
   
3. **Nucleophilic Substitution:**
   - **Reagents:** CH₃-CH₂-Br (ethyl bromide)
   - **Product:** The alkoxide reacts with ethyl bromide to form an ether linkage, resulting in an extended carbon chain structure.

4. **Friedel-Crafts Acylation:**
   - **Reagents:** CH₃OH (methanol), AlCl₃ (aluminum chloride)
   - **Mechanism:** The aromatic ring undergoes acylation. Methoxy groups are introduced, and carbonyl chloride acts as the electrophile, with AlCl₃ as a catalyst.

5. **Final Product Formation:**
   - The final structure includes the methoxy groups on the aromatic ring with the extended carbon chain, completing the synthesis pathway.

**Diagram Explanation:**

- **Initial and Final Structures:** The transformation begins with an aldehyde structure and ends with a complex aromatic ether compound.
- **Chemical Structures:** Each intermediate stage is illustrated with structural formulas, denoting the specific transformations through colored arrows and annotations to highlight changes.
- **Reaction Conditions:** Each step clearly shows the required reagents and conditions necessary to achieve the desired conversion.

This synthesis illustrates the strategic application of organic reaction mechanisms and reagents to achieve complex molecular transformations efficiently.
Transcribed Image Text:**Title: Synthesis Pathway for Chemical Transformation** --- **Objective:** Provide a plausible synthesis for the given overall chemical transformation. Include all necessary workup steps, reagents, and draw each intermediate structure. **Transformation Overview:** The transformation begins with an aldehyde and converts it into a methoxy substituted aromatic compound with an extended carbon chain. **Step-by-Step Synthesis:** 1. **Grignard Addition:** - **Reagents:** 1) PhMgBr (phenylmagnesium bromide), 2) H₃O⁺ - **Intermediate Structure:** After Grignard addition, the resulting intermediate is a secondary alcohol with a phenyl group. 2. **Alkoxide Formation:** - **Reagents:** Na⁺ O⁻ H (sodium hydroxide) - **Process:** The hydroxyl group is deprotonated to form an alkoxide ion. 3. **Nucleophilic Substitution:** - **Reagents:** CH₃-CH₂-Br (ethyl bromide) - **Product:** The alkoxide reacts with ethyl bromide to form an ether linkage, resulting in an extended carbon chain structure. 4. **Friedel-Crafts Acylation:** - **Reagents:** CH₃OH (methanol), AlCl₃ (aluminum chloride) - **Mechanism:** The aromatic ring undergoes acylation. Methoxy groups are introduced, and carbonyl chloride acts as the electrophile, with AlCl₃ as a catalyst. 5. **Final Product Formation:** - The final structure includes the methoxy groups on the aromatic ring with the extended carbon chain, completing the synthesis pathway. **Diagram Explanation:** - **Initial and Final Structures:** The transformation begins with an aldehyde structure and ends with a complex aromatic ether compound. - **Chemical Structures:** Each intermediate stage is illustrated with structural formulas, denoting the specific transformations through colored arrows and annotations to highlight changes. - **Reaction Conditions:** Each step clearly shows the required reagents and conditions necessary to achieve the desired conversion. This synthesis illustrates the strategic application of organic reaction mechanisms and reagents to achieve complex molecular transformations efficiently.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
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