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REACTION INTERMEDIATES

REACTION INTERMEDIATES.

ferdinand-anderson
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REACTION INTERMEDIATES

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  1. REACTION INTERMEDIATES The product cannot be obtaned by direct addition of the diene on ther dienophile, because the cyclottatetraene double bonds involved are not conjugated, as the Diels-Alder reaction requests. Moreover, the double bonds must have a cis-planar conformation, as in this case: and this is impossible in the lowest energy conformation of cycloottateetraene

  2. On the basis of the structure of the product, the hypotesys is that before the addition of ther dienophile a tautomerization of the cyclootattetraene to an intermediate possessing the necessary structural features takes place. The reaction becames: The corresponding kinetic law is d[P]/dt = k2 [I][TCE] That with the steady-state approximation can be rewritten as d[I]/dt = 0 = k1 [COT] – k-1 [I] - k2 [I][TCE] from which we have

  3. then using [I] in the rate law that is In experimental conditions of pseudo-first order d[P]/dt = kobs [COT] and considering that the experimental equation is equal tothe teorical one this is a line equation in which kobs is reported on kobs/[TCE] and the INTERCETTA is k1 value and the slope is k-1/k1

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