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Complete the drawing of the product of the Diels-Alder reaction, ignoring stereochemistry

Chemistry Dec 29, 2020

Complete the drawing of the product of the Diels-Alder reaction, ignoring stereochemistry. The Diels- Alder reaction between butadiene and dimethyl maleatc yields a ring structure, as shown in the product below Complete the structure by drawing any missing bonds and indicating the stereochemistry of the new stereocenters.

Expert Solution

1.Explanation | Common mistakes | Hint for next step

From the given starting materials, the diene and dienophile is identified.

Then, the [4+2] cycloaddition of those parts of the substrates takes place to give the cyclohexa-1,4-diene substrate as product.

To write the structure of the product in the Diels-Alder reaction just move the three pairs of electrons in the diene (two pairs) and dienophile (one pair). Because of movement of electrons, two new single bonds are formed between the terminal carbon atoms of the diene and dienophile, a double bond is formed at the C2-C3 part of diene and one bond is removed in the dienophile.

The product of the Diels-Alder reaction is drawn applying the above rules.

2.

From the given starting materials, the diene and dienophile is identified.

Then, the [4+2] cycloaddition of those parts of the substrates takes to give the cyclohexene substrate as product.

To write the structure of the product in the Diels-Alder reaction just the move three pairs of electrons in the diene (two pairs) and dienophile (one pair). Because of movement of electrons, two new bonds are formed between the terminal carbon atoms of the diene and dienophile, a double bond is formed at the C2-C3 part of diene and one bond is removed in the dienophile.

According to endo rule, the electron withdrawing group in dienophile should occupy the endo position in the product thus the COOCH3group is in the endo to the cyclohexene ring.

please see the attached file for complete solution

The product of the Diels-Alder reaction is drawn applying the above rules.

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