For each pericyclic reaction below, write in the box whether the reaction is Diels-Alder, Electrocyclic, or Sigmatropic. Then fill in all mechanistic arrows for the forward (left to right) reaction.
For each pericyclic reaction below, write in the box whether the reaction is Diels-Alder, Electrocyclic, or Sigmatropic. Then fill in all mechanistic arrows for the forward (left to right) reaction.
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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Question
![**Title: Understanding Pericyclic Reactions**
**Introduction**
Pericyclic reactions are a class of concerted chemical reactions that proceed via a cyclic transition state. They are generally categorized into three types: Diels-Alder, Electrocyclic, and Sigmatropic. Below are examples of these reactions. Your task is to identify each reaction type and draw the mechanistic arrows for the forward reaction.
**Example Reactions**
1. **Diels-Alder Reaction**
- **Description**: This reaction typically involves a [4+2] cycloaddition between a conjugated diene and a dienophile, producing a cyclohexene ring.
- **Reaction**:
```
[Image: Benzene ring arrow to cyclohexane]
```
- **Mechanism**: Draw arrows indicating the movement of electrons forming the new σ-bonds from the π-bonds of the diene and the dienophile.
2. **Electrocyclic Reaction**
- **Description**: These reactions involve the conversion of a π-bonded system into a σ-bonded ring via a conrotatory or disrotatory motion.
- **Reaction**:
```
[Image: Cyclopentadiene arrow to pentane with π-bond]
```
- **Mechanism**: Draw arrows showing the rotation and reorganization of π-electrons forming the new σ-bonds.
3. **Sigmatropic Rearrangements**
- **Description**: Sigmatropic shifts involve the migration of a σ-bonded substituent from one position to another within the molecule, maintaining the π-electron system.
- **Reaction**:
```
[Image: Allyl vinyl ether arrow to cyclohexane with π-bond and substituent]
```
- **Mechanism**: Illustrate the shift of the σ-bond and the reorganization of the π-electrons.
**Practice Task**
For each pericyclic reaction shown below, identify the reaction type (Diels-Alder, Electrocyclic, or Sigmatropic) and draw the mechanistic arrows for the forward (left to right) reaction.
1. Cyclohexadiene to cyclohexane
```
[Image with blank box]
```
2. Cyclopentadiene with a π-bond to pentane with a π-bond and substituent
```
[Image with blank box](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F6746fa6f-1856-443b-addc-ecae5d9da9b9%2F8e26f1ac-e65a-4254-a187-e571d1646f7a%2Ffwcnwnl_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Title: Understanding Pericyclic Reactions**
**Introduction**
Pericyclic reactions are a class of concerted chemical reactions that proceed via a cyclic transition state. They are generally categorized into three types: Diels-Alder, Electrocyclic, and Sigmatropic. Below are examples of these reactions. Your task is to identify each reaction type and draw the mechanistic arrows for the forward reaction.
**Example Reactions**
1. **Diels-Alder Reaction**
- **Description**: This reaction typically involves a [4+2] cycloaddition between a conjugated diene and a dienophile, producing a cyclohexene ring.
- **Reaction**:
```
[Image: Benzene ring arrow to cyclohexane]
```
- **Mechanism**: Draw arrows indicating the movement of electrons forming the new σ-bonds from the π-bonds of the diene and the dienophile.
2. **Electrocyclic Reaction**
- **Description**: These reactions involve the conversion of a π-bonded system into a σ-bonded ring via a conrotatory or disrotatory motion.
- **Reaction**:
```
[Image: Cyclopentadiene arrow to pentane with π-bond]
```
- **Mechanism**: Draw arrows showing the rotation and reorganization of π-electrons forming the new σ-bonds.
3. **Sigmatropic Rearrangements**
- **Description**: Sigmatropic shifts involve the migration of a σ-bonded substituent from one position to another within the molecule, maintaining the π-electron system.
- **Reaction**:
```
[Image: Allyl vinyl ether arrow to cyclohexane with π-bond and substituent]
```
- **Mechanism**: Illustrate the shift of the σ-bond and the reorganization of the π-electrons.
**Practice Task**
For each pericyclic reaction shown below, identify the reaction type (Diels-Alder, Electrocyclic, or Sigmatropic) and draw the mechanistic arrows for the forward (left to right) reaction.
1. Cyclohexadiene to cyclohexane
```
[Image with blank box]
```
2. Cyclopentadiene with a π-bond to pentane with a π-bond and substituent
```
[Image with blank box
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