0244Pb14an-10.cwk (WP)

0244Pb14an-10.cwk (WP) - electrons, 6 and 10, but one can t...

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Answers to Problem 14, Chemistry 0244 - 2010 SG, p 373, book p 646ff Part (d): If the orbital picture is as shown below, we have a cyclic, fully conjugated system with six pi electrons - looks aromatic to me. Will it be super-stable? There is no reason to think so - that carbene carbon is electron-deficient, and thus, the molecule will probably be very reactive. We might say that we expect it to be stable, for a carbene . six π electrons in the cycle For the first three bridged molecules, the problem is that the short bridge means that the pi system cannot overlap optimally. The first two compounds have the right number of pi
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Unformatted text preview: electrons, 6 and 10, but one can t be certain that there will be real conjugation (overlap). This question doesn t arise in the third molecule because it has the wrong number of electrons anyway, and can t be aromatic. = overlap problem overlap problem In the crazy selenium molecule, those nonbonding electrons will be in an n = 4 p orbital. Will overlap with the adjacent 2 orbitals on carbon be good? No. Will it be aromatic? Yes, if overlap is good enough to provide the six-electron circuit; no if it s not....
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Spring '10 term at NYU.

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