Q 14-14-62 E

Question

Dimethyl butynedioate undergoes a Diels-Alder reaction with (2E,4E)-2,4-hexadiene. Show the structure and stereochemistry of the product.

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Answer

1Diels-Alder reaction

Diels-Alder reaction is an important organic reaction which includes a substituted alkene in the form of a dienophile and a conjugated diene. It proceeds via concerted mechanism (simultaneous bond breaking and bond formation). Diels alder reaction generates a 6 membered ring.

It is a pericyclic reaction between a conjugated diene and a dienophile. The reaction is stereospecefic i.e., the cis dienophile will give cis stereochemistry in product and trans dienophile will generate product with trans stereochemistry.

Diels-Alder Reaction

2Diels-Alder Reaction

Diene is an organic compound which comprises of two or more double bonds separated by a single bond while dienophile is a diene loving compound or ( a substituted alkene with electron withdrawing group). When the interaction between them, occurs a transition state without any additional energy barrier, is obtained.

3Diels-Alder reaction of Dimethyl butynedioate and (2E,4E)-2,4-hexadiene

Diels-Alder Reaction

Q 14-14-61 E

Q 14-14-63 E

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