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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![### Predicting Major Products in Reactions
**Problem Statement:**
For each of the following reactions, predict the major product.
---
**Reaction 1:**
**Starting Material:**
A carboxylic acid with the structure:
\[ \text{CH}_3\text{CH}_2\text{C(=O)OH} \]
**Reagents and Conditions:**
1. Thionyl chloride (\(\text{SOCl}_2\))
2. Excess ethylamine (\(\text{H}_2\text{NCH}_2\text{CH}_3\))
**Hints:**
- The reaction sequence typically starts with converting the carboxylic acid to an acyl chloride using \(\text{SOCl}_2\).
- The acyl chloride is then treated with excess amine to form an amide.
---
**Reaction 2:**
**Starting Material:**
An aromatic ketone with a methoxy group:
\[ \text{MeO-C}_6\text{H}_4-\text{C(=O)CH}_3 \]
**Reagent:**
m-Chloroperoxybenzoic acid (\(m\text{CPBA}\))
**Hints:**
- This reaction often involves oxidation to convert the ketone into an ester or an epoxide formation.
- Consider the possibility of forming a Baeyer-Villiger oxidation product.
---
**Reaction 3:**
**Starting Material:**
A methyl ester:
\[ \text{CH}_3\text{C(=O)OMe} \]
**Reagents and Conditions:**
1. Lithium diisopropylamide (LDA)
2. A methoxy acrylate (\(\text{MeO-C(=O)CH=CH}_2\))
3. Hydrochloric acid and water (\(\text{HCl}, \text{H}_2\text{O}\))
**Hints:**
- LDA is a strong base that can deprotonate the alpha position of an ester, initiating an alpha-alkylation reaction.
- The enolate anion can then attack the electrophilic alkene.
- Consider any subsequent hydrolysis or additional reactions with \(\text{HCl}\) and \(\text{H}_2\text{O}\).
---
**Discussion:**
Understanding these reactions involves applying concepts of organic synthesis, such as nucleoph](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fa1308c18-827c-41a1-b2ec-8a88ef0ba574%2F66375dbc-b7dd-403a-88c0-af01a41e01c7%2F7uudest_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Predicting Major Products in Reactions
**Problem Statement:**
For each of the following reactions, predict the major product.
---
**Reaction 1:**
**Starting Material:**
A carboxylic acid with the structure:
\[ \text{CH}_3\text{CH}_2\text{C(=O)OH} \]
**Reagents and Conditions:**
1. Thionyl chloride (\(\text{SOCl}_2\))
2. Excess ethylamine (\(\text{H}_2\text{NCH}_2\text{CH}_3\))
**Hints:**
- The reaction sequence typically starts with converting the carboxylic acid to an acyl chloride using \(\text{SOCl}_2\).
- The acyl chloride is then treated with excess amine to form an amide.
---
**Reaction 2:**
**Starting Material:**
An aromatic ketone with a methoxy group:
\[ \text{MeO-C}_6\text{H}_4-\text{C(=O)CH}_3 \]
**Reagent:**
m-Chloroperoxybenzoic acid (\(m\text{CPBA}\))
**Hints:**
- This reaction often involves oxidation to convert the ketone into an ester or an epoxide formation.
- Consider the possibility of forming a Baeyer-Villiger oxidation product.
---
**Reaction 3:**
**Starting Material:**
A methyl ester:
\[ \text{CH}_3\text{C(=O)OMe} \]
**Reagents and Conditions:**
1. Lithium diisopropylamide (LDA)
2. A methoxy acrylate (\(\text{MeO-C(=O)CH=CH}_2\))
3. Hydrochloric acid and water (\(\text{HCl}, \text{H}_2\text{O}\))
**Hints:**
- LDA is a strong base that can deprotonate the alpha position of an ester, initiating an alpha-alkylation reaction.
- The enolate anion can then attack the electrophilic alkene.
- Consider any subsequent hydrolysis or additional reactions with \(\text{HCl}\) and \(\text{H}_2\text{O}\).
---
**Discussion:**
Understanding these reactions involves applying concepts of organic synthesis, such as nucleoph
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