Using the resonance energies of benzene andnaphthalene, explain why Diels-Alder

Question

   Using the resonance energies of benzene andnaphthalene, explain why Diels-Alder reactions of anthracene takeplace at the center ring, not on one of the end rings. (resonance energies: benzene 36 kcal/mole; naphthalene 60kcal/mole; anthracene 84 kcal/mole)    Using the resonance energies of benzene andnaphthalene, explain why Diels-Alder reactions of anthracene takeplace at the center ring, not on one of the end rings. (resonance energies: benzene 36 kcal/mole; naphthalene 60kcal/mole; anthracene 84 kcal/mole)

Explanation / Answer

When the diels alder reaction takes place at the center ring, it leaves 2 benzene rings intact in the adduct giving it the lowest resonance energy possibly. This is the most stable way for the reaction to occur.

Here is some material from the university of missouri that explains this a little bit further.

http://www.google.com/url?sa=t&rct=j&q=&esrc=s&source=web&cd=1&ved=0CCgQFjAA&url=http%3A%2F%2Fwww.chem.missouri.edu%2Fchem2120%2FDiels.doc&ei=VVQeU9b6GOjIyAG87IB4&usg=AFQjCNHpzJ32V6HQlm6l84ps9vXC7GwVWg&sig2=oep8Sc5fY4h4Cjx_lRNIwA&bvm=bv.62788935,d.aWc

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