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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![**Title: Reaction Mechanisms and Resonance Structures**
**Instruction:**
Be sure to answer all parts.
**Question:**
Determine a stepwise mechanism for the following reaction that illustrates why two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a nucleophile under SN1 reaction conditions, even though it is a 1° allylic halide.
---
**Chemical Reaction:**
1-bromohex-2-ene + CH₃OH → Substitution products + HBr
![Reaction Diagram](image)
---
**Part 1:**
**Question:**
The first step in the reaction proceeds according to which mechanism?
**Options:**
- **CHOICE 1:** \( \small \text{CH}_3\text{CH}_2\text{CH} = \text{CHCH}_2\text{Br} \)
- **CHOICE 2:** \( \small \text{CH}_3\text{CH}_2\text{CHCH}_2^+ + \text{Br}^- \)
---
**Part 2 out of 5:**
**Task:**
Draw the missing resonance contributor.
**Structure:**
\( \small \text{CH}_3\text{CH}_2\text{CH} = \text{CHCH}_2^+ \)
\[ \xrightarrow{\text{missing resonance contributor}} \]
- Given drawing: \( \small \text{CH}_3\text{CH}_2\text{CH} - \text{CH} = \text{CH}_2 + \text{Br}^- \)
---
**Options:**
- **Edit Structure:** Create the detailed structure for resonance.
---
**Navigation:**
- **Check my work** button
- **Next part** button
---
**Explanations:**
1. **Chemical Reaction Overview:**
- The reaction involves the transformation of 1-bromohex-2-ene in the presence of a nucleophile (CH₃OH), leading to the formation of substitution products and HBr.
2. **Mechanism Explanation:**
- **Choice 1** and **Choice 2** represent possible intermediates, with the correct resonance structure leading to better understanding of the SN1 reaction mechanism.
3. **Resonance Diagram:**
- Shows contribution of various resonance forms to stabilize the carbocation intermediate.
Utilize](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fa8ba3a71-d749-40cb-a922-6232b6a4906b%2Fda651143-9f85-4a24-98bf-7e657562268b%2Fdnp5vhc_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Title: Reaction Mechanisms and Resonance Structures**
**Instruction:**
Be sure to answer all parts.
**Question:**
Determine a stepwise mechanism for the following reaction that illustrates why two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a nucleophile under SN1 reaction conditions, even though it is a 1° allylic halide.
---
**Chemical Reaction:**
1-bromohex-2-ene + CH₃OH → Substitution products + HBr
![Reaction Diagram](image)
---
**Part 1:**
**Question:**
The first step in the reaction proceeds according to which mechanism?
**Options:**
- **CHOICE 1:** \( \small \text{CH}_3\text{CH}_2\text{CH} = \text{CHCH}_2\text{Br} \)
- **CHOICE 2:** \( \small \text{CH}_3\text{CH}_2\text{CHCH}_2^+ + \text{Br}^- \)
---
**Part 2 out of 5:**
**Task:**
Draw the missing resonance contributor.
**Structure:**
\( \small \text{CH}_3\text{CH}_2\text{CH} = \text{CHCH}_2^+ \)
\[ \xrightarrow{\text{missing resonance contributor}} \]
- Given drawing: \( \small \text{CH}_3\text{CH}_2\text{CH} - \text{CH} = \text{CH}_2 + \text{Br}^- \)
---
**Options:**
- **Edit Structure:** Create the detailed structure for resonance.
---
**Navigation:**
- **Check my work** button
- **Next part** button
---
**Explanations:**
1. **Chemical Reaction Overview:**
- The reaction involves the transformation of 1-bromohex-2-ene in the presence of a nucleophile (CH₃OH), leading to the formation of substitution products and HBr.
2. **Mechanism Explanation:**
- **Choice 1** and **Choice 2** represent possible intermediates, with the correct resonance structure leading to better understanding of the SN1 reaction mechanism.
3. **Resonance Diagram:**
- Shows contribution of various resonance forms to stabilize the carbocation intermediate.
Utilize
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