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What is the product of the following reaction? ОН 1) excess MeMgBr 2) H2O _OH ? OH

What is the product of the following reaction? ОН 1) excess MeMgBr 2) H2O _OH ? OH

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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### Reaction Question The problem presented is to determine the product of a chemical reaction. Here is the detailed breakdown of the reaction process: #### Reaction Overview The reaction involves a starting compound of a carbon chain with an ester group (a carbon-oxygen double bond and a single bond to another oxygen). The reagents added sequentially are: 1. Excess **MeMgBr** (Methylmagnesium bromide) 2. **H₂O** (Water) #### Reaction Mechanism The MeMgBr reagent is a Grignard reagent, which is known for its ability to add carbon atoms to a compound. It will react with the ester group: 1. **Nucleophilic addition**: The methyl group from MeMgBr attacks the electrophilic carbon of the ester carbonyl group, leading to the formation of an intermediate where the carbonyl oxygen becomes negatively charged. 2. **Tetrahedral intermediate formation**: The intermediate collapses, releasing the alkoxy group (OCH₃ in this case) and forming a ketone. 3. **Further reaction with excess MeMgBr**: The newly formed ketone is attacked by the excess MeMgBr, leading to another nucleophilic addition, resulting in a tertiary alcohol after further reaction with water. #### Products The possible products from this reaction are represented by the structural formulas shown below the main reaction equation. The major product expected can be deduced based on reaction knowledge: - From left to right, these structures represent: 1. A tertiary alcohol with an additional carbon coming from the Grignard reagent. 2. A primary alcohol chain. 3. A secondary alcohol chain. 4. An alternative tertiary alcohol. 5. A ketone. The correct product is the tertiary alcohol where the carbon chain has been extended due to the addition of two methyl groups from the Grignard reagent. ### Conclusion Given the conditions of the reaction (excess MeMgBr and water), the most likely product is the tertiary alcohol resulting from the addition of two methyl groups to the initial compound after hydrolysis.
Transcribed Image Text:### Reaction Question The problem presented is to determine the product of a chemical reaction. Here is the detailed breakdown of the reaction process: #### Reaction Overview The reaction involves a starting compound of a carbon chain with an ester group (a carbon-oxygen double bond and a single bond to another oxygen). The reagents added sequentially are: 1. Excess **MeMgBr** (Methylmagnesium bromide) 2. **H₂O** (Water) #### Reaction Mechanism The MeMgBr reagent is a Grignard reagent, which is known for its ability to add carbon atoms to a compound. It will react with the ester group: 1. **Nucleophilic addition**: The methyl group from MeMgBr attacks the electrophilic carbon of the ester carbonyl group, leading to the formation of an intermediate where the carbonyl oxygen becomes negatively charged. 2. **Tetrahedral intermediate formation**: The intermediate collapses, releasing the alkoxy group (OCH₃ in this case) and forming a ketone. 3. **Further reaction with excess MeMgBr**: The newly formed ketone is attacked by the excess MeMgBr, leading to another nucleophilic addition, resulting in a tertiary alcohol after further reaction with water. #### Products The possible products from this reaction are represented by the structural formulas shown below the main reaction equation. The major product expected can be deduced based on reaction knowledge: - From left to right, these structures represent: 1. A tertiary alcohol with an additional carbon coming from the Grignard reagent. 2. A primary alcohol chain. 3. A secondary alcohol chain. 4. An alternative tertiary alcohol. 5. A ketone. The correct product is the tertiary alcohol where the carbon chain has been extended due to the addition of two methyl groups from the Grignard reagent. ### Conclusion Given the conditions of the reaction (excess MeMgBr and water), the most likely product is the tertiary alcohol resulting from the addition of two methyl groups to the initial compound after hydrolysis.
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