Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

Question
**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.
expand button
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.
Expert Solution
Check Mark
Step 1: Given reaction and mechanism

The given reaction is Chemistry homework question answer, step 1, image 1

And, the given reaction mechanism also shown below

Chemistry homework question answer, step 1, image 2

We have to determine all the reaction intermediates.

Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY