For the given reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction. CH3OH + NAOCH3 + NaCI 4. or acetone OCH, SN1, CH3OH SN2, CH3OH SN1, acetone SN2, acetone
For the given reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction. CH3OH + NAOCH3 + NaCI 4. or acetone OCH, SN1, CH3OH SN2, CH3OH SN1, acetone SN2, acetone
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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![**Educational Content: Reaction Mechanisms and Solvent Effects**
**Reaction Description:**
For the given reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.
**Reaction Equation:**
\[
\text{CH}_3\text{CH}_2\text{Cl} + \text{NaOCH}_3 \xrightarrow{\text{CH}_3\text{OH or acetone}} \text{CH}_3\text{CH}_2\text{OCH}_3 + \text{NaCl}
\]
**Multiple Choice Options:**
- \( \text{S}_\text{N}1, \text{CH}_3\text{OH} \)
- \( \text{S}_\text{N}2, \text{CH}_3\text{OH} \)
- \( \text{S}_\text{N}1, \text{acetone} \)
- \( \text{S}_\text{N}2, \text{acetone} \)
**Explanation of Concepts:**
1. **Alkyl Halides:**
- Alkyl halides (e.g., \(\text{CH}_3\text{CH}_2\text{Cl}\)) are reactive compounds that typically undergo nucleophilic substitution reactions.
2. **Nucleophilic Substitution Reactions:**
- **\( \text{S}_\text{N}1 (Unimolecular Nucleophilic Substitution):** Involves a two-step mechanism where the leaving group departs first, forming a carbocation intermediate, followed by nucleophilic attack.
- **\( \text{S}_\text{N}2 (Bimolecular Nucleophilic Substitution):** Involves a one-step mechanism where the nucleophile attacks the substrate and displaces the leaving group simultaneously.
3. **Solvent Effects:**
- **\(\text{CH}_3\text{OH} (Methanol):** Polar protic solvent, can stabilize ions and favor \( \text{S}_\text{N}1 \) reactions.
- **Acetone:** Polar aprotic solvent, does not stabilize ions as effectively and often favors \( \text{S}_\text{N}2 \) reactions.
**Guidance](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8f2ba725-83de-43a2-959b-aa0d30d09f08%2Fa6fa9d39-d573-44f6-83d0-0877be5fdeef%2Fl7agk9j_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Educational Content: Reaction Mechanisms and Solvent Effects**
**Reaction Description:**
For the given reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction.
**Reaction Equation:**
\[
\text{CH}_3\text{CH}_2\text{Cl} + \text{NaOCH}_3 \xrightarrow{\text{CH}_3\text{OH or acetone}} \text{CH}_3\text{CH}_2\text{OCH}_3 + \text{NaCl}
\]
**Multiple Choice Options:**
- \( \text{S}_\text{N}1, \text{CH}_3\text{OH} \)
- \( \text{S}_\text{N}2, \text{CH}_3\text{OH} \)
- \( \text{S}_\text{N}1, \text{acetone} \)
- \( \text{S}_\text{N}2, \text{acetone} \)
**Explanation of Concepts:**
1. **Alkyl Halides:**
- Alkyl halides (e.g., \(\text{CH}_3\text{CH}_2\text{Cl}\)) are reactive compounds that typically undergo nucleophilic substitution reactions.
2. **Nucleophilic Substitution Reactions:**
- **\( \text{S}_\text{N}1 (Unimolecular Nucleophilic Substitution):** Involves a two-step mechanism where the leaving group departs first, forming a carbocation intermediate, followed by nucleophilic attack.
- **\( \text{S}_\text{N}2 (Bimolecular Nucleophilic Substitution):** Involves a one-step mechanism where the nucleophile attacks the substrate and displaces the leaving group simultaneously.
3. **Solvent Effects:**
- **\(\text{CH}_3\text{OH} (Methanol):** Polar protic solvent, can stabilize ions and favor \( \text{S}_\text{N}1 \) reactions.
- **Acetone:** Polar aprotic solvent, does not stabilize ions as effectively and often favors \( \text{S}_\text{N}2 \) reactions.
**Guidance
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