Mg-Br: .CH3 H,C CH3 H,C H,C-Mg-Br: CH3 H,C H3C H,C `CH, H,C

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

Can you assist me in identifying what I did wrong in this mechanism? Thank you.

 

The image illustrates the reaction mechanism of a Grignard reagent with a carbonyl compound, leading to the formation of a cyclic ester or lactone. Below is the explanation of each step in the mechanism:

1. **Top Left Box:**
   - The Grignard reagent, represented by `CH3-MgBr`, is shown reacting with the carbonyl group of an ester. This is a classic nucleophilic addition where the carbon atom of the Grignard reagent attacks the electrophilic carbon of the carbonyl group.
   - The arrows indicate the movement of electrons: an arrow from the Grignard reagent's carbon to the carbonyl carbon signifies the nucleophilic attack, and another arrow shows the electron pair from the carbonyl double bond shifting to the oxygen atom.

2. **Top Right Box:**
   - The carbonyl carbon has been attacked by the Grignard reagent, resulting in a tetrahedral intermediate. The carbon-oxygen double bond has been shifted to a single bond, with the oxygen carrying a negative charge (represented by the dots and negative sign).
   - The intermediate highlights the transfer of the MgBr from the Grignard reagent to contribute to the stabilization of the oxygen's negative charge.
   - Arrows also indicate that the next step involves elimination of the leaving group, potentially leading to ring closure.

3. **Bottom Right Box:**
   - Following the elimination of the leaving group (the alcohol part of the ester), a cyclic structure begins to form. 
   - Arrows demonstrate the movement of electrons facilitating this cyclization. The oxygen atom in the intermediate bonds to a neighboring carbon atom, closing the ring and forming a five-membered lactone.

4. **Bottom Left Box:**
   - The final product is a cyclic ester or lactone, indicated by the pentagon structure with an oxygen atom incorporated into the ring.
   - The structure has returned to a stable state, with all electron pairs accounted for and no remaining negative charges.

This sequence of reactions showcases the transformation of an ester into a cyclic ester via a Grignard reaction, emphasizing nucleophilic addition, intermediate formation, and ring closure dynamics.
Transcribed Image Text:The image illustrates the reaction mechanism of a Grignard reagent with a carbonyl compound, leading to the formation of a cyclic ester or lactone. Below is the explanation of each step in the mechanism: 1. **Top Left Box:** - The Grignard reagent, represented by `CH3-MgBr`, is shown reacting with the carbonyl group of an ester. This is a classic nucleophilic addition where the carbon atom of the Grignard reagent attacks the electrophilic carbon of the carbonyl group. - The arrows indicate the movement of electrons: an arrow from the Grignard reagent's carbon to the carbonyl carbon signifies the nucleophilic attack, and another arrow shows the electron pair from the carbonyl double bond shifting to the oxygen atom. 2. **Top Right Box:** - The carbonyl carbon has been attacked by the Grignard reagent, resulting in a tetrahedral intermediate. The carbon-oxygen double bond has been shifted to a single bond, with the oxygen carrying a negative charge (represented by the dots and negative sign). - The intermediate highlights the transfer of the MgBr from the Grignard reagent to contribute to the stabilization of the oxygen's negative charge. - Arrows also indicate that the next step involves elimination of the leaving group, potentially leading to ring closure. 3. **Bottom Right Box:** - Following the elimination of the leaving group (the alcohol part of the ester), a cyclic structure begins to form. - Arrows demonstrate the movement of electrons facilitating this cyclization. The oxygen atom in the intermediate bonds to a neighboring carbon atom, closing the ring and forming a five-membered lactone. 4. **Bottom Left Box:** - The final product is a cyclic ester or lactone, indicated by the pentagon structure with an oxygen atom incorporated into the ring. - The structure has returned to a stable state, with all electron pairs accounted for and no remaining negative charges. This sequence of reactions showcases the transformation of an ester into a cyclic ester via a Grignard reaction, emphasizing nucleophilic addition, intermediate formation, and ring closure dynamics.
**Reaction Mechanism Overview**

In this reaction, we observe the conversion of a β-keto ester into a cyclopentane derivative using a Grignard reagent. 

**Reactants:**

1. **β-Keto Ester**: The starting material is a compound with two carbonyl groups; one is a ketone and the other is an ester. 
   - Structure: CH₃COCH₂CH₂COOEt
   - Functional Groups: 
     - Ketone group: located at the third carbon from the left. 
     - Ester group: located at the fifth carbon from the left, with an ethyl group as the alkoxy component.

2. **Grignard Reagent**: Ethylmagnesium bromide (EtMgBr).
   - This reagent is known for nucleophilic properties, introducing an ethyl group to the carbonyl carbon.

**Product:**

- A cyclopentane derivative is formed, featuring:
  - A five-membered ring with:
    - An oxygen atom as part of the cyclic structure.
    - A ketone group remains at one carbon on the ring.
  - Two methyl groups attached to adjacent carbons in the ring.

**Mechanism Explanation:**

1. **Nucleophilic Addition**:
   - The Grignard reagent attacks the carbonyl carbon of the ester group.
   - This leads to the formation of a tetrahedral alkoxide intermediate.

2. **Intramolecular Nucleophilic Substitution**:
   - The alkoxide intermediate facilitates a nucleophilic attack on the carbonyl of the ketone group within the same molecule.
   - This results in cyclization and the formation of the five-membered ring structure.

3. **Workup**:
   - Protonation of the enolate or alkoxide intermediate yields the final cyclic ketone product.

This reaction showcases a practical application of Grignard reagents in organic synthesis, particularly in constructing cyclic structures from linear precursors.
Transcribed Image Text:**Reaction Mechanism Overview** In this reaction, we observe the conversion of a β-keto ester into a cyclopentane derivative using a Grignard reagent. **Reactants:** 1. **β-Keto Ester**: The starting material is a compound with two carbonyl groups; one is a ketone and the other is an ester. - Structure: CH₃COCH₂CH₂COOEt - Functional Groups: - Ketone group: located at the third carbon from the left. - Ester group: located at the fifth carbon from the left, with an ethyl group as the alkoxy component. 2. **Grignard Reagent**: Ethylmagnesium bromide (EtMgBr). - This reagent is known for nucleophilic properties, introducing an ethyl group to the carbonyl carbon. **Product:** - A cyclopentane derivative is formed, featuring: - A five-membered ring with: - An oxygen atom as part of the cyclic structure. - A ketone group remains at one carbon on the ring. - Two methyl groups attached to adjacent carbons in the ring. **Mechanism Explanation:** 1. **Nucleophilic Addition**: - The Grignard reagent attacks the carbonyl carbon of the ester group. - This leads to the formation of a tetrahedral alkoxide intermediate. 2. **Intramolecular Nucleophilic Substitution**: - The alkoxide intermediate facilitates a nucleophilic attack on the carbonyl of the ketone group within the same molecule. - This results in cyclization and the formation of the five-membered ring structure. 3. **Workup**: - Protonation of the enolate or alkoxide intermediate yields the final cyclic ketone product. This reaction showcases a practical application of Grignard reagents in organic synthesis, particularly in constructing cyclic structures from linear precursors.
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Nomenclature of Organic Compounds
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