Diels-Alder Reaction: Predict Product | 65 Characters

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In summary, the product of the Diels-Alder reaction between a 4-carbon diene and methyl 2-butenoate would result in the formation of a cyclic compound with a double bond between the second and third carbon after the COO- group. The diene should be in the Z configuration and the methyl ester and methyl group should be in the same orientation, either up or down, in a syn fashion. The term "endo" is not applicable in this system.
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thE3nigma
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Hi,

This is not a homework question but something I found within my textbook. I just wanted to understand a solution they gave to the problem.

The question is:
Predict the product of the following Diels-Alder reaction:

The structures of two molecules, a diene (4 carbons long) and a methyl butyrate (methyl butanoate).

The answer has the methyl ester and H atom popping out of the book. I just wanted to confirm that it would not be wrong if it was drawn with the methyl ester and H atom going into the book would it? I do not think this is an endo substituent in this case.
 
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  • #2
Is methyl butyrate a dienophile? Not in my books.
 
  • #3
Sorry, I misspelled the molecules name. It is methyl 2-butenoate (I believe that is the correct name). There is a double bond between the second and third carbon after the COO- group.
 
  • #4
... and is the diene cyclic? Is that methyl-2-butenoate E or Z?
 
  • #5
It is Z, the diene is not cyclic.
 
  • #6
Endo isn't the right term to use in this system. http://www.iupac.org/goldbook/E02094.pdf"

Both the methyl ester and the methyl group should be either up or down... syn fashion.
 
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1. What is the Diels-Alder reaction and how does it work?

The Diels-Alder reaction is a chemical reaction between a diene and a dienophile to form a cyclohexene ring. It involves the breaking and forming of bonds to create a new molecule. This reaction typically occurs through a concerted mechanism, where all bond changes happen simultaneously.

2. What are the reactants and products in a Diels-Alder reaction?

The reactants in a Diels-Alder reaction are a diene, which is a molecule with two double bonds, and a dienophile, which is a molecule with one double bond. The product is a cyclohexene ring, with the diene and dienophile fused together.

3. How can you predict the product of a Diels-Alder reaction?

The product of a Diels-Alder reaction can be predicted by looking at the structure of the reactants. The diene and dienophile must have a specific orientation and geometry for the reaction to occur. Additionally, the product will have one more carbon atom than the reactants, and the new double bond will be formed between the two previously double-bonded carbons.

4. What factors affect the rate of a Diels-Alder reaction?

The rate of a Diels-Alder reaction can be affected by several factors, including the reactivity of the diene and dienophile, the presence of electron-withdrawing or electron-donating groups on the reactants, and the reaction temperature. The reaction rate can also be influenced by the solvent used and the concentration of the reactants.

5. Can the Diels-Alder reaction be used in organic synthesis?

Yes, the Diels-Alder reaction is commonly used in organic synthesis to create complex molecules with multiple rings and functional groups. It is a powerful tool for creating new carbon-carbon bonds and is widely used in the pharmaceutical and materials industries.

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