What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-met O weak nucleophile in a protic solvent weak nucleophile in an aprotic solvent O strong nucleophile in a protic solvent O strong nucleophile in an aprotic solvent
What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-met O weak nucleophile in a protic solvent weak nucleophile in an aprotic solvent O strong nucleophile in a protic solvent O strong nucleophile in an aprotic solvent
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 23E
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![### Understanding SN1 Reactions: Conditions and Mechanisms
**Question:** What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-methylbutane?
#### Answer Choices:
- **Option 1:** weak nucleophile in a protic solvent
- **Option 2:** weak nucleophile in an aprotic solvent
- **Option 3:** strong nucleophile in a protic solvent
- **Option 4:** strong nucleophile in an aprotic solvent
### Explanation:
An SN1 reaction (unimolecular nucleophilic substitution) typically involves two main steps:
1. **Formation of a carbocation intermediate:** The leaving group (bromine in this case) dissociates from the substrate, forming a carbocation.
2. **Nucleophilic attack:** The nucleophile attacks the carbocation to form the final product.
#### Key Factors that Favor SN1 Reactions:
1. **Type of Solvent:**
- **Protic Solvents:** These solvents stabilize the carbocation intermediate via hydrogen bonding and solvation, making it easier for the leaving group to dissociate.
2. **Strength of the Nucleophile:**
- **Weak Nucleophile:** Since the rate-determining step of an SN1 reaction is the formation of the carbocation (which does not involve the nucleophile), a weak nucleophile is sufficient for the subsequent step.
From the above factors, it's clear that an SN1 reaction is favored by **a weak nucleophile in a protic solvent**. Therefore:
### Correct Answer:
- **Option 1:** weak nucleophile in a protic solvent
This educational insight underlines the importance of understanding the reaction conditions that favor specific reaction mechanisms in organic chemistry.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fa4b8199f-1785-4bf8-892f-b1973e07d452%2Ff443c70d-e0f3-49bd-b1de-21340797c1ab%2Fq1w7mc_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Understanding SN1 Reactions: Conditions and Mechanisms
**Question:** What set of reaction conditions would favor an SN1 reaction on 2-bromo-3-methylbutane?
#### Answer Choices:
- **Option 1:** weak nucleophile in a protic solvent
- **Option 2:** weak nucleophile in an aprotic solvent
- **Option 3:** strong nucleophile in a protic solvent
- **Option 4:** strong nucleophile in an aprotic solvent
### Explanation:
An SN1 reaction (unimolecular nucleophilic substitution) typically involves two main steps:
1. **Formation of a carbocation intermediate:** The leaving group (bromine in this case) dissociates from the substrate, forming a carbocation.
2. **Nucleophilic attack:** The nucleophile attacks the carbocation to form the final product.
#### Key Factors that Favor SN1 Reactions:
1. **Type of Solvent:**
- **Protic Solvents:** These solvents stabilize the carbocation intermediate via hydrogen bonding and solvation, making it easier for the leaving group to dissociate.
2. **Strength of the Nucleophile:**
- **Weak Nucleophile:** Since the rate-determining step of an SN1 reaction is the formation of the carbocation (which does not involve the nucleophile), a weak nucleophile is sufficient for the subsequent step.
From the above factors, it's clear that an SN1 reaction is favored by **a weak nucleophile in a protic solvent**. Therefore:
### Correct Answer:
- **Option 1:** weak nucleophile in a protic solvent
This educational insight underlines the importance of understanding the reaction conditions that favor specific reaction mechanisms in organic chemistry.
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