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1. На0, кон 2. Н,О, НС он HO, HO. p-cresol chloroacetic acid p-methylphenoxyacetic acid

1. На0, кон 2. Н,О, НС он HO, HO. p-cresol chloroacetic acid p-methylphenoxyacetic acid

Chemistry
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...
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Draw the reaction mechanism for the Williamson Ether reaction. Cresol is the nucleophilic component of the ether synthesis reaction and chloroacetic acid is the electrophilic component. Due to cresol being weak, a strong nucleophile has to be made before the reaction can begin. A base of KOH is added with cresol so that nucleophile can be strong before it is mixed with chloroacetic acid. 

### Resonance Stabilization of Phenoxide Ion **Reaction Overview:** - **Phenol (Weak Nucleophile)**: The structure on the far left is phenol, which consists of a benzene ring bonded to a hydroxyl group (OH). - **KOH Reaction**: The arrow indicates the reaction of phenol with potassium hydroxide (KOH) to form the phenoxide ion. - **Phenoxide (Stronger Nucleophile)**: Once reacted, phenol becomes phenoxide, which has an oxygen anion (O⁻) indicating a loss of a hydrogen ion (H⁺) from the hydroxyl group. **Resonance Structures:** - The phenoxide ion can be represented by several resonance structures, showcasing the delocalization of the negative charge: 1. The negative charge on the oxygen atom. 2. The negative charge is shared with the ortho and para positions of the benzene ring, indicated by arrows between structures. 3. In each structure, the double-bond character shifts within the benzene ring, maintaining charge distribution. This series of diagrams demonstrates how the phenoxide ion is resonance-stabilized, making it a stronger nucleophile compared to phenol. The ability to delocalize charges across the benzene ring enhances the ion's stability and reactivity.
Transcribed Image Text:### Resonance Stabilization of Phenoxide Ion **Reaction Overview:** - **Phenol (Weak Nucleophile)**: The structure on the far left is phenol, which consists of a benzene ring bonded to a hydroxyl group (OH). - **KOH Reaction**: The arrow indicates the reaction of phenol with potassium hydroxide (KOH) to form the phenoxide ion. - **Phenoxide (Stronger Nucleophile)**: Once reacted, phenol becomes phenoxide, which has an oxygen anion (O⁻) indicating a loss of a hydrogen ion (H⁺) from the hydroxyl group. **Resonance Structures:** - The phenoxide ion can be represented by several resonance structures, showcasing the delocalization of the negative charge: 1. The negative charge on the oxygen atom. 2. The negative charge is shared with the ortho and para positions of the benzene ring, indicated by arrows between structures. 3. In each structure, the double-bond character shifts within the benzene ring, maintaining charge distribution. This series of diagrams demonstrates how the phenoxide ion is resonance-stabilized, making it a stronger nucleophile compared to phenol. The ability to delocalize charges across the benzene ring enhances the ion's stability and reactivity.
**Chemical Reaction: Synthesis of p-Methylphenoxyacetic Acid** In the illustrated chemical reaction, p-cresol reacts with chloroacetic acid to form p-methylphenoxyacetic acid. Below are the details of the reagents and conditions involved in the process: **Reactants:** - **p-Cresol:** An aromatic compound with a hydroxyl group (-OH) attached to a benzene ring. - **Chloroacetic Acid:** A carboxylic acid containing a chlorine atom attached to the alpha carbon. **Reaction Conditions:** 1. The reaction is performed in the presence of water (H₂O) and potassium hydroxide (KOH). 2. This is followed by treatment with water (H₂O) and hydrochloric acid (HCl). **Product:** - **p-Methylphenoxyacetic Acid:** The resulting compound, featuring an ether linkage between the phenolic oxygen of p-cresol and the acetic acid, forming an extended acetic acid derivative. **Diagram Explanation:** - The diagram provides a visual representation of the reaction. Each reactant is connected by an arrow indicating the transformation into the product. - Structural formulas are shown for each compound to detail the chemical structure and changes during the reaction process. This reaction is a fundamental synthetic procedure in organic chemistry, often used to illustrate uses of phenolic compounds in generating ethers and related derivatives.
Transcribed Image Text:**Chemical Reaction: Synthesis of p-Methylphenoxyacetic Acid** In the illustrated chemical reaction, p-cresol reacts with chloroacetic acid to form p-methylphenoxyacetic acid. Below are the details of the reagents and conditions involved in the process: **Reactants:** - **p-Cresol:** An aromatic compound with a hydroxyl group (-OH) attached to a benzene ring. - **Chloroacetic Acid:** A carboxylic acid containing a chlorine atom attached to the alpha carbon. **Reaction Conditions:** 1. The reaction is performed in the presence of water (H₂O) and potassium hydroxide (KOH). 2. This is followed by treatment with water (H₂O) and hydrochloric acid (HCl). **Product:** - **p-Methylphenoxyacetic Acid:** The resulting compound, featuring an ether linkage between the phenolic oxygen of p-cresol and the acetic acid, forming an extended acetic acid derivative. **Diagram Explanation:** - The diagram provides a visual representation of the reaction. Each reactant is connected by an arrow indicating the transformation into the product. - Structural formulas are shown for each compound to detail the chemical structure and changes during the reaction process. This reaction is a fundamental synthetic procedure in organic chemistry, often used to illustrate uses of phenolic compounds in generating ethers and related derivatives.
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