What are the possible products when α-Pinene is treated with B2H6 and H2O2 + NaOH? What is the major product? What if α-Pinene is treated with peroxy acid + THF?
What are the possible products when α-Pinene is treated with B2H6 and H2O2 + NaOH? What is the major product? What if α-Pinene is treated with peroxy acid + THF?
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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What are the possible products when α-Pinene is treated with B2H6 and H2O2 + NaOH? What is the major product?
What if α-Pinene is treated with peroxy acid + THF?
Transcribed Image Text:### 8.17 α-Pinene
**Overview:**
α-Pinene is a compound isolated from pine resin and serves as a primary constituent of turpentine, commonly used as paint thinner. Both enantiomers of α-pinene occur naturally.
**Experiment Description:**
To analyze the enantiomeric excess (% ee) of α-pinene in various spruce trees, the α-pinene was modified through a process called hydroboration-oxidation, focusing on the (–)-enantiomer.
**Procedure:**
1. **Hydroboration Step:**
- Diborane (B₂H₆) was used as an alternative to BH₃∙THF for hydroboration of the alkene.
- Hydroboration can occur from either face of the alkene, leading to two potential diastereomeric products.
- The major product results from an attack on the less hindered face of the alkene.
2. **Oxidation Step:**
- Followed by oxidation using H₂O₂ and NaOH.
**Diagram Explanation:**
- The starting material, (–)-α-Pinene, is depicted with its structural formula showing its bicyclic form with methyl groups.
- The sequence of reactions, first with B₂H₆ and then with H₂O₂, NaOH, is shown with a question mark, indicating the need to determine the structure of the product.
- Challenge: Draw both possible products and predict which diastereomer is the major product.
**Outcome:**
Understanding the reactivity and stereochemistry of α-pinene through this process and predicting the major diastereomer formed.
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