Asked by Rob
Why does the reaction of (Z)-butenedioic acid (fumaric acid) with 1,3-cyclopentadiene
give only one product?
I don't know where to start.
Thanks.
give only one product?
I don't know where to start.
Thanks.
Answers
Answered by
bobpursley
First, your nomenclature. Maleic acid is the cis-(Z)-2-butenedioic acid and fumaric acid is the trans-(E)-2-butenedioic acid. So unsure of your conformation, I will assume Maleic acid.
Maleic acid reacts as a dienophile in the above reaction. cyclopentadiene (obviously) is the diene. A diene and dienophile react in what is known as the Diels-Alder reaction. In this case, since maleic acid is symmetrical, it only adds in one orientation to the diene, giving you a heterocyclic compund with only one possible conformation.
Maleic acid reacts as a dienophile in the above reaction. cyclopentadiene (obviously) is the diene. A diene and dienophile react in what is known as the Diels-Alder reaction. In this case, since maleic acid is symmetrical, it only adds in one orientation to the diene, giving you a heterocyclic compund with only one possible conformation.
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