Draw structural formulas for organic products A and B in the window below. CH3 CH3CHCH₂CH₂l Li pentane A Cul B

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Chapter1: Chemical Foundations
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**Title: Understanding Organolithium and Organocuprate Reactions**

**Objective:** Draw the structural formulas for organic products A and B.

**Reaction Overview:**

1. **Starting Material:**
   - The compound starts with a primary alkyl iodide: 
     - **Structure:** 
       - 2-iodopentane (CH₃CHCH₂CH₂CH₂I)
       - A five-carbon chain with an iodine atom attached to the third carbon.

2. **Step 1: Formation of Organolithium Compound**
   - **Reagents:** Lithium (Li) in pentane solvent.
   - **Process:** 
     - Lithium displaces the iodine atom from the starting material, forming an organolithium compound.
     - **Product A:** An organolithium compound, 2-pentan-2-yl lithium.

3. **Step 2: Reaction with Copper(I) Iodide**
   - **Reagents:** Copper(I) iodide (CuI).
   - **Process:**
     - The organolithium compound reacts with CuI to form a Gilman reagent (lithium dialkylcuprate).
     - **Product B:** The resulting compound is typically used in further reactions to create coupling products. In this context, the focus is on illustrating the conversion through these reagents.

**Conclusion:** Through these steps, students will explore how the organolithium compound is used to form different organocuprate derivatives, emphasizing transformations in organic synthesis. Understanding these reactions provides foundational knowledge for complex organic synthesis and mechanisms.
Transcribed Image Text:**Title: Understanding Organolithium and Organocuprate Reactions** **Objective:** Draw the structural formulas for organic products A and B. **Reaction Overview:** 1. **Starting Material:** - The compound starts with a primary alkyl iodide: - **Structure:** - 2-iodopentane (CH₃CHCH₂CH₂CH₂I) - A five-carbon chain with an iodine atom attached to the third carbon. 2. **Step 1: Formation of Organolithium Compound** - **Reagents:** Lithium (Li) in pentane solvent. - **Process:** - Lithium displaces the iodine atom from the starting material, forming an organolithium compound. - **Product A:** An organolithium compound, 2-pentan-2-yl lithium. 3. **Step 2: Reaction with Copper(I) Iodide** - **Reagents:** Copper(I) iodide (CuI). - **Process:** - The organolithium compound reacts with CuI to form a Gilman reagent (lithium dialkylcuprate). - **Product B:** The resulting compound is typically used in further reactions to create coupling products. In this context, the focus is on illustrating the conversion through these reagents. **Conclusion:** Through these steps, students will explore how the organolithium compound is used to form different organocuprate derivatives, emphasizing transformations in organic synthesis. Understanding these reactions provides foundational knowledge for complex organic synthesis and mechanisms.
Expert Solution
Step 1: Gilman reagent:

Lithium organocuprates, R2CuLi is known as Gilman reagent.  Gilman reagent is very selective for nucleophilic substitution reactions and conjugation addition reactions of the alpha-beta unsaturated carbonyl compound.

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