Part 2 out of 5 Draw the missing resonance contributor. CH₂CH₂CH.CH=CHCH₂ CH₂CH₂CH₂CH=CH-CH₂ + Br Br Br

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...
icon
Related questions
Question
100%
**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
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
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 2 images

Blurred answer
Knowledge Booster
Alkanes and Cycloalkanes
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.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY