Solved Problem 1 (Continued) Predict the products of the following proposed Diels-Alder reactions. OCH3 Solution (Continued) CH30 H CN H + 1,2-relationship (product) CN CH₂0, H H CN 1,3-relationship (not formed)

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Chapter1: Chemical Foundations
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How come for the first screenshot, the 1,3-relationship is a minor product but with the second screenshot, the 1,3-relationship does not even exist? What is the difference?

**Solved Problem 1 (Continued)**

**Predict the products of the following proposed Diels–Alder reactions.**

- A diene with an OCH₃ substituent is reacting with a dienophile that has a CN group.

**Solution (Continued)**

- The reaction results in two possible regioisomeric products:

  1. **1,2-relationship (product):**
     - The OCH₃ group is adjacent to the CN group on the same side of the newly formed cyclohexene ring.
     - This is the main product of the reaction.

  2. **1,3-relationship (not formed):**
     - The OCH₃ group and the CN group are separated by one carbon on the cyclohexene ring.
     - This configuration does not form under the reaction conditions. 

In the diagrams, substituents are shown using wedge and dash notation to indicate stereochemistry.
Transcribed Image Text:**Solved Problem 1 (Continued)** **Predict the products of the following proposed Diels–Alder reactions.** - A diene with an OCH₃ substituent is reacting with a dienophile that has a CN group. **Solution (Continued)** - The reaction results in two possible regioisomeric products: 1. **1,2-relationship (product):** - The OCH₃ group is adjacent to the CN group on the same side of the newly formed cyclohexene ring. - This is the main product of the reaction. 2. **1,3-relationship (not formed):** - The OCH₃ group and the CN group are separated by one carbon on the cyclohexene ring. - This configuration does not form under the reaction conditions. In the diagrams, substituents are shown using wedge and dash notation to indicate stereochemistry.
**Solved Problem 1 (Continued)**

**Predict the products of the following proposed Diels–Alder reactions.**

Two chemical structures are shown:

1. The first structure is a conjugated diene represented by a six-membered ring with an OCH₃ group attached.
2. The second structure is a dienophile with a cyano group (CN) attached.

**Solution (Continued)**

The diagram illustrates the possible products of the Diels–Alder reaction between these two structures:

1. **1,2-relationship (product):** 
   - The product is a six-membered ring where one end of the diene and the dienophile have formed new bonds. 
   - The OCH₃ and CN groups are attached to the newly formed cyclohexene ring in a 1,2-relationship, indicating the proximity of the substituents on adjacent carbon atoms. This product is shown with wedges and dashes indicating stereochemistry, where the OCH₃ group and one H atom are both facing away from the viewer, and the CN group and the other H atom are facing towards the viewer.

2. **1,3-relationship (not formed):** 
   - A hypothetical six-membered ring with the OCH₃ and CN groups attached in a 1,3-relationship is also shown to indicate possible but unformed structural isomers. In this structure, the OCH₃ group and one H atom face away from the viewer, while the CN group and the other H atom face towards the viewer.

The diagram helps illustrate the regioselectivity of the Diels–Alder reaction, showing which stereochemical configurations form predominately under these reaction conditions.
Transcribed Image Text:**Solved Problem 1 (Continued)** **Predict the products of the following proposed Diels–Alder reactions.** Two chemical structures are shown: 1. The first structure is a conjugated diene represented by a six-membered ring with an OCH₃ group attached. 2. The second structure is a dienophile with a cyano group (CN) attached. **Solution (Continued)** The diagram illustrates the possible products of the Diels–Alder reaction between these two structures: 1. **1,2-relationship (product):** - The product is a six-membered ring where one end of the diene and the dienophile have formed new bonds. - The OCH₃ and CN groups are attached to the newly formed cyclohexene ring in a 1,2-relationship, indicating the proximity of the substituents on adjacent carbon atoms. This product is shown with wedges and dashes indicating stereochemistry, where the OCH₃ group and one H atom are both facing away from the viewer, and the CN group and the other H atom are facing towards the viewer. 2. **1,3-relationship (not formed):** - A hypothetical six-membered ring with the OCH₃ and CN groups attached in a 1,3-relationship is also shown to indicate possible but unformed structural isomers. In this structure, the OCH₃ group and one H atom face away from the viewer, while the CN group and the other H atom face towards the viewer. The diagram helps illustrate the regioselectivity of the Diels–Alder reaction, showing which stereochemical configurations form predominately under these reaction conditions.
Expert Solution
Step 1

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. 

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