The following reaction combines concepts from ch 18 and ch 16. Draw a detailed mechanism for this reaction. 1. NaNH2 (excess) 2. racemic

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**Reaction Mechanism Problem Description:**

**Question 4:**

The following reaction combines concepts from Chapter 18 and Chapter 16. *Draw a detailed mechanism for this reaction.*

**Reaction Scheme:**

The reaction starts with a benzyl methyl ether on the left, undergoing two key steps.

1. **Step 1:** The reaction uses an excess of sodium amide (NaNH₂) as a reagent.
2. **Step 2:** The intermediate from Step 1 is treated with an alkene ketone compound.

The final product on the right is a bicyclic compound with an appended methyl group and an aldehyde functional group, labeled "racemic," indicating the presence of both enantiomers in equal proportions. 

**Diagram Explanation:**

- **Starting Material:** A benzyl methyl ether.
- **Intermediate Steps:** These involve reactions facilitated by NaNH₂, which is a strong base, suggesting the generation of an anion or deprotonation.
- **Final Product:** This involves ring formation and/or rearrangement to form a bicyclic structure with chiral centers, leading to the racemic nature of the product.
Transcribed Image Text:**Reaction Mechanism Problem Description:** **Question 4:** The following reaction combines concepts from Chapter 18 and Chapter 16. *Draw a detailed mechanism for this reaction.* **Reaction Scheme:** The reaction starts with a benzyl methyl ether on the left, undergoing two key steps. 1. **Step 1:** The reaction uses an excess of sodium amide (NaNH₂) as a reagent. 2. **Step 2:** The intermediate from Step 1 is treated with an alkene ketone compound. The final product on the right is a bicyclic compound with an appended methyl group and an aldehyde functional group, labeled "racemic," indicating the presence of both enantiomers in equal proportions. **Diagram Explanation:** - **Starting Material:** A benzyl methyl ether. - **Intermediate Steps:** These involve reactions facilitated by NaNH₂, which is a strong base, suggesting the generation of an anion or deprotonation. - **Final Product:** This involves ring formation and/or rearrangement to form a bicyclic structure with chiral centers, leading to the racemic nature of the product.
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