(39 of 41) According to the reaction mechanism in Question 37, please identify all reaction intermediates. A H₂O I 1) CH3MgBr 2) H3O+ CH3 B OH X H D F OH X™ 5 CH3 E H G -H
(39 of 41) According to the reaction mechanism in Question 37, please identify all reaction intermediates. A H₂O I 1) CH3MgBr 2) H3O+ CH3 B OH X H D F OH X™ 5 CH3 E H G -H
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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Transcribed Image Text:**Reaction Mechanism and Intermediates**
**Question Context:**
According to the reaction mechanism in Question 37, please identify all reaction intermediates.
**Reagents and Conditions:**
1) \( \text{CH}_3\text{MgBr} \)
2) \( \text{H}_3\text{O}^+ \)
**Target Product:**
The reaction leads to the formation of a tertiary alcohol (displayed as having an OH group attached to a tert-butyl group).
**Reaction Steps and Intermediates:**
1. **Intermediate A:**
- The mechanism begins with a ketone structure, where the carbonyl carbon is electrophilic.
2. **Intermediate B:**
- The \( \text{CH}_3\text{MgBr} \) performs a nucleophilic attack on the carbonyl carbon, breaking the \(C=O\) bond and forming an alkoxide ion.
3. **Intermediate C:**
- Rearrangement and stabilization of the alkoxide ion occur. The oxygen carries a negative charge represented with a lone pair, indicating its role as an anion.
4. **Intermediate D:**
- The alkoxide ion undergoes protonation facilitated by \( \text{H}_3\text{O}^+ \), leading to the formation of the alcohol intermediate.
5. **Intermediate E:**
- The carbonyl oxygen gains a proton (from \( \text{H}_3\text{O}^+ \)), resulting in an oxonium ion configuration.
6. **Intermediate F:**
- A rearrangement/transformation occurs, likely showing the pathway toward stabilization and final product formation.
7. **Intermediate G:**
- Further interaction with water (\( \text{H}_2\text{O} \)) leading to a stable hydration step that is characteristic in the final alcohol formation.
8. **Intermediate H:**
- Final deprotonation step to form the stable tertiary alcohol.
9. **Intermediate I:**
- The complete structure of the tertiary alcohol is shown. Any excess water interactions stabilize the reaction.
**Visualization:**
The diagrammatic sequence describes a multi-step reaction mechanism typical in Grignard reactions with ketones, resulting in alcohol products.
**Note:** The positions are numbered to depict electron/lone pair movements and structural changes throughout the reaction pathway.
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