When cyclopentadiene reacts with tetracyanoethene yields,1,3-dicyclopentadienyl.
The reaction between cyclopentadiene and tetracyanoethene is an example of a Diels-Alder reaction, a type of reaction in which a diene (a molecule with two double bonds) reacts with a dienophile (a molecule with two double bonds) to give a cyclic product. In this case, the diene is cyclopentadiene and the dienophile is tetracyanoethene.
The reaction starts with the formation of a cyclic transition state. In this state, the two double bonds of the diene react with the two double bonds of the dienophile, forming a four-membered ring.
After this, the two molecules rearrange and form a six-membered ring, with the tetracyanoethene molecule forming a bridge between the two cyclopentadiene molecules. This rearrangement is accompanied by the release of two molecules of carbon dioxide.
The end result is a compound known as a 1,3-dicyclopentadienyl cation, which has two cyclopentadiene molecules bonded to a central tetracyanoethene molecule. This compound is thermodynamically very stable, and thus is the major product of the reaction. The image of the structure of the product is attached below.
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