Predict the product(s) and show the complete electron-pushing mecha- nism for each of the following dissolving metal reductions. (a) H3CC=CCH₂CH3 (b) (c) CECH Li NH3 ND3 -C=C-CH3 Li NH3

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**Title: Dissolving Metal Reductions: Electron-Pushing Mechanisms**

**Objective:**
Predict the product(s) and illustrate the complete electron-pushing mechanisms for each dissolving metal reduction reaction.

**Reactions:**

1. **Reaction (a):**
   - **Substrate:** \( \text{H}_3\text{C} \equiv \text{CCH}_2\text{CH}_3 \)
   - **Reagents:** Li / \( \text{NH}_3 \)
   - **Goal:** Demonstrate the electron-pushing mechanism to predict the product(s) formed.

2. **Reaction (b):**
   - **Substrate:** ![Isopropenyl acetylene structure](https://example.com/aromatic_structure.png) (Text representation)
   - **Reagents:** Li / \( \text{ND}_3 \)
   - **Goal:** Show the step-by-step mechanism and predict the resulting structure(s).

3. **Reaction (c):**
   - **Substrate:** ![Phenylacetylene structure](https://example.com/phenylacetylene_structure.png) (Text representation)
   - **Reagents:** Li / \( \text{NH}_3 \)
   - **Goal:** Illustrate the electron transitions and identify the final products.

**Mechanism Details:**
- **Electron Transfer:** Lithium donates an electron, creating an anion and a radical species.
- **Protonation:** The radical is protonated by the solvent (ammonia), converting it to another reactive intermediate.
- **Final Reduction:** The process repeats, leading to the fully reduced alkene.

This exercise focuses on understanding and visualizing the electron flow and transformations during the chemical reactions in the context of dissolving metal reductions. Each reaction should be explored thoroughly to predict the accurate structure of the organometallic product formed.
Transcribed Image Text:**Title: Dissolving Metal Reductions: Electron-Pushing Mechanisms** **Objective:** Predict the product(s) and illustrate the complete electron-pushing mechanisms for each dissolving metal reduction reaction. **Reactions:** 1. **Reaction (a):** - **Substrate:** \( \text{H}_3\text{C} \equiv \text{CCH}_2\text{CH}_3 \) - **Reagents:** Li / \( \text{NH}_3 \) - **Goal:** Demonstrate the electron-pushing mechanism to predict the product(s) formed. 2. **Reaction (b):** - **Substrate:** ![Isopropenyl acetylene structure](https://example.com/aromatic_structure.png) (Text representation) - **Reagents:** Li / \( \text{ND}_3 \) - **Goal:** Show the step-by-step mechanism and predict the resulting structure(s). 3. **Reaction (c):** - **Substrate:** ![Phenylacetylene structure](https://example.com/phenylacetylene_structure.png) (Text representation) - **Reagents:** Li / \( \text{NH}_3 \) - **Goal:** Illustrate the electron transitions and identify the final products. **Mechanism Details:** - **Electron Transfer:** Lithium donates an electron, creating an anion and a radical species. - **Protonation:** The radical is protonated by the solvent (ammonia), converting it to another reactive intermediate. - **Final Reduction:** The process repeats, leading to the fully reduced alkene. This exercise focuses on understanding and visualizing the electron flow and transformations during the chemical reactions in the context of dissolving metal reductions. Each reaction should be explored thoroughly to predict the accurate structure of the organometallic product formed.
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