Chapter3: Mechanisms
Section: Chapter Questions
Problem 28EQ
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Question 7
Transcribed Image Text:**Title: Reaction Mechanism for Grignard Reagent with Epoxide**
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**Objective:**
To understand and draw the mechanism of the reaction between a Grignard reagent and an epoxide leading to alcohol formation.
**Reaction Overview:**
1. **Reagents and Conditions:**
- Grignard reagent: represented as an alkyl chain with a magnesium bromide group (MgBr).
- Epoxide: a three-membered cyclic ether.
- Water (H₂O) is used in a subsequent step.
2. **Products:**
- An alcohol with an extended carbon chain.
**Mechanism Details:**
- **Step 1: Nucleophilic Attack by the Grignard Reagent**
- The carbon attached to the MgBr in the Grignard reagent acts as a nucleophile.
- It attacks the less hindered carbon atom of the epoxide ring.
- This attack opens the epoxide ring, forming a new carbon-carbon bond while pushing the electrons from the oxygen to create an alkoxide.
- **Step 2: Protonation**
- In the presence of water (step 2), the alkoxide ion is protonated to form the final alcohol product.
- The oxygen atom of the opened epoxide is converted to an -OH group.
**Diagram Explanation:**
- On the left, the Grignard reagent is depicted with the MgBr group and the alkyl chain.
- The middle shows the epoxide: a triangle with an oxygen atom at the top vertex.
- An arrow points from the Grignard reagent to the epoxide, indicating the nucleophilic attack.
- On the right, the product is shown as an extended alkyl chain terminating with an -OH group, illustrating the formation of the alcohol.
This reaction exemplifies how organometallic chemistry can be utilized to form alcohols from simple reagents by extending carbon skeletons. Understanding this mechanism is crucial for mastering synthetic strategies in organic chemistry.
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