Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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**Reaction Mechanism and Product Prediction**

1. **Instruction:**
   - Show the detailed, step-by-step mechanism using the curvy arrow formalism.
   - Predict the structure of the product from the following reaction.

2. **Reaction Overview:**
   - **Reactant:** A ketone with a side-chain (molecule on the left with a carbonyl group connected to an ethyl chain).
   - **Reagents:**
     1. Grignard Reagent: R-MgBr in diethyl ether (Et₂O).
     2. Acid Workup: H₃O⁺.

3. **Mechanistic Steps:**
   - **Step 1:** The Grignard reagent (R-MgBr) reacts with the carbonyl carbon of the ketone, resulting in nucleophilic addition. The magnesium bromide (MgBr) helps stabilize the negative charge developed on the oxygen.
   - **Step 2:** Protonation of the alkoxide intermediate occurs via the acidic workup (H₃O⁺), leading to the formation of an alcohol group.

4. **Product Structure:**
   - The resulting product is an alcohol with a newly introduced carbon chain (R group from the Grignard reagent).

**Diagram Explanation:**
- The diagram shows the skeletal structure of the ketone and the path of the reaction: attacking the carbonyl carbon, followed by the protonation step. Curved arrows indicate electron movement, showing the conversion of the ketone to an alcohol.
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Transcribed Image Text:**Reaction Mechanism and Product Prediction** 1. **Instruction:** - Show the detailed, step-by-step mechanism using the curvy arrow formalism. - Predict the structure of the product from the following reaction. 2. **Reaction Overview:** - **Reactant:** A ketone with a side-chain (molecule on the left with a carbonyl group connected to an ethyl chain). - **Reagents:** 1. Grignard Reagent: R-MgBr in diethyl ether (Et₂O). 2. Acid Workup: H₃O⁺. 3. **Mechanistic Steps:** - **Step 1:** The Grignard reagent (R-MgBr) reacts with the carbonyl carbon of the ketone, resulting in nucleophilic addition. The magnesium bromide (MgBr) helps stabilize the negative charge developed on the oxygen. - **Step 2:** Protonation of the alkoxide intermediate occurs via the acidic workup (H₃O⁺), leading to the formation of an alcohol group. 4. **Product Structure:** - The resulting product is an alcohol with a newly introduced carbon chain (R group from the Grignard reagent). **Diagram Explanation:** - The diagram shows the skeletal structure of the ketone and the path of the reaction: attacking the carbonyl carbon, followed by the protonation step. Curved arrows indicate electron movement, showing the conversion of the ketone to an alcohol.
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