Devise a detailed mechanism for formation of the major product of the elimination reaction below.  Draw curved arrows to show electron reorganization for the mechanism step below. Make the ends of your arrows specify the origin and destination of reorganizing electrons.

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

Devise a detailed mechanism for formation of the major product of the elimination reaction below. 

Draw curved arrows to show electron reorganization for the mechanism step below. Make the ends of your arrows specify the origin and destination of reorganizing electrons.

 

The image shows a chemical reaction involving several organic compounds. Below is a detailed explanation of each component in the reaction:

**Chemical Structures:**

1. **Reactant on the left:**
   - The structure is a sulfonate ester.
   - The central group is a sulfonate (SO₃) attached to a carbon chain.
   - One of the carbon chains is a tert-butyl group (a carbon atom connected to three methyl groups).
   - A benzene ring (aromatic) is attached, with a methyl group (CH₃) at the para-position relative to the sulfonate.

2. **Middle Reactants:**
   - Sodium methoxide (Na⁺O⁻CH₃) is shown. It's an ionic compound with sodium (Na⁺) and methoxide ion (O⁻CH₃).
   - Methanol (CH₃OH) is depicted, an alcohol with one hydroxyl group (OH) attached to a methyl group (CH₃).

**Reaction Arrow:**
- A right-facing arrow indicates the progression from reactants to products.

This type of illustration is typical in organic chemistry to demonstrate reactions such as nucleophilic substitutions, where methoxide might act as a nucleophile in the presence of the sulfonate ester.
Transcribed Image Text:The image shows a chemical reaction involving several organic compounds. Below is a detailed explanation of each component in the reaction: **Chemical Structures:** 1. **Reactant on the left:** - The structure is a sulfonate ester. - The central group is a sulfonate (SO₃) attached to a carbon chain. - One of the carbon chains is a tert-butyl group (a carbon atom connected to three methyl groups). - A benzene ring (aromatic) is attached, with a methyl group (CH₃) at the para-position relative to the sulfonate. 2. **Middle Reactants:** - Sodium methoxide (Na⁺O⁻CH₃) is shown. It's an ionic compound with sodium (Na⁺) and methoxide ion (O⁻CH₃). - Methanol (CH₃OH) is depicted, an alcohol with one hydroxyl group (OH) attached to a methyl group (CH₃). **Reaction Arrow:** - A right-facing arrow indicates the progression from reactants to products. This type of illustration is typical in organic chemistry to demonstrate reactions such as nucleophilic substitutions, where methoxide might act as a nucleophile in the presence of the sulfonate ester.
**Title: Mechanistic Elucidation for Elimination Reaction**

**Objective:**
Devise a detailed mechanism for the formation of the major product of the elimination reaction depicted below.

**Reaction Details:**

- **Substrate**: 2,3-dimethyl-2-butyl tosylate (OTs group)
- **Reagent**: Sodium methoxide (\(\text{CH}_3\text{ONa}\))
- **Solvent**: Methanol (\(\text{CH}_3\text{OH}\))

**Instructions:**
Draw curved arrows to demonstrate electron reorganization for the mechanism step below. Ensure the arrows clearly specify the origin and destination of the reorganizing electrons.

**Diagram Explanation:**

- The substrate with a tosylate leaving group is set to undergo elimination.
- Sodium methoxide serves as both the base and nucleophile.
- Methanol functions as the solvent, facilitating the reaction conditions.

**Mechanism Overview:**

1. **Base Abstraction:**
   - Methoxide ion (\(\text{CH}_3\text{O}^-\)) acts as a base.
   - It abstracts a proton from the beta-carbon adjacent to the carbon bearing the tosylate group.

2. **Formation of Double Bond:**
   - The electrons from the C-H bond form a double bond between the alpha and beta carbons.
  
3. **Departure of Leaving Group:**
   - The resulting negative charge facilitates the departure of the tosylate leaving group, completing the elimination mechanism.

**Result:**
Formation of the major alkene product through an E2 elimination mechanism in a single concerted step. 

This mechanistic insight provides an understanding of electron flow and structural rearrangement during the reaction process.
Transcribed Image Text:**Title: Mechanistic Elucidation for Elimination Reaction** **Objective:** Devise a detailed mechanism for the formation of the major product of the elimination reaction depicted below. **Reaction Details:** - **Substrate**: 2,3-dimethyl-2-butyl tosylate (OTs group) - **Reagent**: Sodium methoxide (\(\text{CH}_3\text{ONa}\)) - **Solvent**: Methanol (\(\text{CH}_3\text{OH}\)) **Instructions:** Draw curved arrows to demonstrate electron reorganization for the mechanism step below. Ensure the arrows clearly specify the origin and destination of the reorganizing electrons. **Diagram Explanation:** - The substrate with a tosylate leaving group is set to undergo elimination. - Sodium methoxide serves as both the base and nucleophile. - Methanol functions as the solvent, facilitating the reaction conditions. **Mechanism Overview:** 1. **Base Abstraction:** - Methoxide ion (\(\text{CH}_3\text{O}^-\)) acts as a base. - It abstracts a proton from the beta-carbon adjacent to the carbon bearing the tosylate group. 2. **Formation of Double Bond:** - The electrons from the C-H bond form a double bond between the alpha and beta carbons. 3. **Departure of Leaving Group:** - The resulting negative charge facilitates the departure of the tosylate leaving group, completing the elimination mechanism. **Result:** Formation of the major alkene product through an E2 elimination mechanism in a single concerted step. This mechanistic insight provides an understanding of electron flow and structural rearrangement during the reaction process.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Ammonium Salts
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
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