Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter18: Aromaticity
Section: Chapter Questions
Problem 7CTQ
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Question
Show how you would prepare each of the following compounds using a Diels-Alder reaction:

Transcribed Image Text:**Title: Diels-Alder Reaction for Compound Synthesis**
**Question 5:** Show how you would prepare each of the following compounds using a Diels-Alder reaction:
**Compound Illustrations:**
1. **Compound 1:**
Structure: A benzene ring bonded to a carbonyl group (C=O) and a methyl group (CH₃).
2. **Compound 2:**
Structure: A bicyclic structure with two cyano groups (CN) attached to the end of the central bridge.
**Guidance for Synthesis:**
- **Diels-Alder Reaction Overview:**
The Diels-Alder reaction is a chemical reaction between a conjugated diene and a dienophile to form a cyclohexene system. This reaction is widely used for constructing six-membered rings.
- **Example Pathways:**
- **For Compound 1:**
- Consider using a conjugated diene like 1,3-butadiene.
- A possible dienophile could be acrolein or methacrolein to introduce the carbonyl group.
- **For Compound 2:**
- Use simple dienes like cyclopentadiene.
- Employ maleonitrile or a similar dienophile to introduce the cyano groups.
Experiment and adapt the reaction conditions to optimize yield and selectivity for each specific compound.
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