5. Show how you would prepare each of the following compounds using a Diels-Alder reaction: CH3 CN CN

Organic Chemistry: A Guided Inquiry
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Author:Andrei Straumanis
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Chapter18: Aromaticity
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Show how you would prepare each of the following compounds using a Diels-Alder reaction:

**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.
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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