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(44) Ⓒ This grinard reaction. does NOT proceed as onaan Shane The Obtenined. 0 organic products mort WILL ACTUALLY be please lust the mechanisms used Br 1. Myl ether 2. Å 3. dilized th+ on

(44) Ⓒ This grinard reaction. does NOT proceed as onaan Shane The Obtenined. 0 organic products mort WILL ACTUALLY be please lust the mechanisms used Br 1. Myl ether 2. Å 3. dilized th+ on

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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**Grignard Reaction Mechanism and Product Analysis** In this chemical analysis, we are exploring a Grignard reaction that does not proceed as originally anticipated. The task is to identify the organic product that will actually be obtained and to list the mechanisms involved in the process. **Initial Reaction Setup:** - Starting compound: a molecule with a bromine (Br) substituent attached to a carbon chain with a ketone (C=O) group (butanoyl bromide structure). **Reagents and Conditions:** 1. **Methylmagnesium bromide (CH₃MgBr) in ether:** This Grignard reagent is intended to initiate the reaction. 2. **Diluted H⁺ (acidic workup):** Aqueous acid is used to protonate the intermediate, leading to the final product. **Actual Product Formation:** - Despite the initial setup, the actual product contains an alcohol (OH) group on the carbon that initially held the bromine substituent. - The final molecule is a carbon chain with both a ketone group and a secondary alcohol group. **Reaction Mechanism Overview:** 1. **Nucleophilic Addition:** - The Grignard reagent (CH₃MgBr) acts as a nucleophile, attacking the electrophilic carbonyl carbon of the ketone group in the starting molecule. 2. **Formation of Alkoxide Intermediate:** - The oxygen, having acquired a negative charge, forms an alkoxide intermediate. 3. **Protonation and Hydrolysis:** - In the presence of diluted acid, the alkoxide intermediate is protonated, transforming it into a secondary alcohol. This analysis illustrates the importance of understanding reaction conditions and mechanisms to predict actual outcomes in organic synthesis.
Transcribed Image Text:**Grignard Reaction Mechanism and Product Analysis** In this chemical analysis, we are exploring a Grignard reaction that does not proceed as originally anticipated. The task is to identify the organic product that will actually be obtained and to list the mechanisms involved in the process. **Initial Reaction Setup:** - Starting compound: a molecule with a bromine (Br) substituent attached to a carbon chain with a ketone (C=O) group (butanoyl bromide structure). **Reagents and Conditions:** 1. **Methylmagnesium bromide (CH₃MgBr) in ether:** This Grignard reagent is intended to initiate the reaction. 2. **Diluted H⁺ (acidic workup):** Aqueous acid is used to protonate the intermediate, leading to the final product. **Actual Product Formation:** - Despite the initial setup, the actual product contains an alcohol (OH) group on the carbon that initially held the bromine substituent. - The final molecule is a carbon chain with both a ketone group and a secondary alcohol group. **Reaction Mechanism Overview:** 1. **Nucleophilic Addition:** - The Grignard reagent (CH₃MgBr) acts as a nucleophile, attacking the electrophilic carbonyl carbon of the ketone group in the starting molecule. 2. **Formation of Alkoxide Intermediate:** - The oxygen, having acquired a negative charge, forms an alkoxide intermediate. 3. **Protonation and Hydrolysis:** - In the presence of diluted acid, the alkoxide intermediate is protonated, transforming it into a secondary alcohol. This analysis illustrates the importance of understanding reaction conditions and mechanisms to predict actual outcomes in organic synthesis.
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