7. For the following reactions of dienes, please draw the 1,2-product and the 1,4-product. Also, please choose one reaction to draw the reaction mechanisms highlighting how both addition products are formed. 1. H3C. ? + ? 1,2-Product 1,4-Product HBr (1 eq) 2. ? ? + Br2 (1 eq.) - 1,2-Product 1,4-Product 3. ? + ? 1,2-Product 1,4-Product + HBr (1 eq.) 4. CH2 ? ? + Br2 CH2 (1 eq) 1,2-Product 1,4-Product
7. For the following reactions of dienes, please draw the 1,2-product and the 1,4-product. Also, please choose one reaction to draw the reaction mechanisms highlighting how both addition products are formed. 1. H3C. ? + ? 1,2-Product 1,4-Product HBr (1 eq) 2. ? ? + Br2 (1 eq.) - 1,2-Product 1,4-Product 3. ? + ? 1,2-Product 1,4-Product + HBr (1 eq.) 4. CH2 ? ? + Br2 CH2 (1 eq) 1,2-Product 1,4-Product
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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![### Diene Addition Reactions
**Exercise:**
7. For the following reactions of dienes, please draw the 1,2-product and the 1,4-product. Additionally, select one reaction to illustrate the reaction mechanisms, highlighting how both addition products are formed.
**Reactions:**
1.
\[
\chemfig{H_3C-[1]-[2]HCR-[1]-[?]-|H_3} \quad
\longrightarrow \quad (1,2-\text{Product}) \quad + \quad (1,4-\text{Product})
\]
2.
\[
\chemfig{*6\erase\polycycle} \quad + \quad \ce{Br2 (1 eq.)}
\quad \longrightarrow \quad (1,2-\text{Product}) \quad + \quad (1,4-\text{Product})
\]
3.
\[
\chemfig{*6\polycycle} \quad + \quad \ce{HBr (1 eq.)}
\quad \longrightarrow \quad (1,2-\text{Product}) \quad + \quad (1,4-\text{Product})
\]
4.
\[
\chemfig{*\chain\HIT\polycycle} \quad + \quad \ce{Br2 (1 eq.)}
\quad \longrightarrow \quad (1,2-\text{Product}) \quad + \quad (1,4-\text{Product})
\]
### Detailed Reaction Mechanism
**Example Reaction Mechanism: 1,3-Butadiene with HBr**
**Step 1: Formation of Allylic Carbocation**
1. **Initial Electrophilic Attack:**
- The diene reacts with HBr.
- The double bond attacks the hydrogen leading to a carbocation intermediate.
2. **Resonance Stabilization:**
- The intermediate can shift to form an allylic carbocation, allowing for resonance stabilization.
**Step 2: Formation of Products**
1. **1,2-Addition Product (Direct Addition to Adjacent Carbon):**
- The bromide ion attacks the carbocation directly adjacent to where the proton added.
2. **1,4-Addition Product (Addition Across the Diene):**
-](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F86fb4fea-474a-4bf3-af54-6f23562d8d8b%2F3f791db4-2209-4722-a7c9-70a48d41a66b%2F17c1ddx_processed.jpeg&w=3840&q=75)
Transcribed Image Text:### Diene Addition Reactions
**Exercise:**
7. For the following reactions of dienes, please draw the 1,2-product and the 1,4-product. Additionally, select one reaction to illustrate the reaction mechanisms, highlighting how both addition products are formed.
**Reactions:**
1.
\[
\chemfig{H_3C-[1]-[2]HCR-[1]-[?]-|H_3} \quad
\longrightarrow \quad (1,2-\text{Product}) \quad + \quad (1,4-\text{Product})
\]
2.
\[
\chemfig{*6\erase\polycycle} \quad + \quad \ce{Br2 (1 eq.)}
\quad \longrightarrow \quad (1,2-\text{Product}) \quad + \quad (1,4-\text{Product})
\]
3.
\[
\chemfig{*6\polycycle} \quad + \quad \ce{HBr (1 eq.)}
\quad \longrightarrow \quad (1,2-\text{Product}) \quad + \quad (1,4-\text{Product})
\]
4.
\[
\chemfig{*\chain\HIT\polycycle} \quad + \quad \ce{Br2 (1 eq.)}
\quad \longrightarrow \quad (1,2-\text{Product}) \quad + \quad (1,4-\text{Product})
\]
### Detailed Reaction Mechanism
**Example Reaction Mechanism: 1,3-Butadiene with HBr**
**Step 1: Formation of Allylic Carbocation**
1. **Initial Electrophilic Attack:**
- The diene reacts with HBr.
- The double bond attacks the hydrogen leading to a carbocation intermediate.
2. **Resonance Stabilization:**
- The intermediate can shift to form an allylic carbocation, allowing for resonance stabilization.
**Step 2: Formation of Products**
1. **1,2-Addition Product (Direct Addition to Adjacent Carbon):**
- The bromide ion attacks the carbocation directly adjacent to where the proton added.
2. **1,4-Addition Product (Addition Across the Diene):**
-
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