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Dolbier HW Solutions 255 - 249 CONJUGATION IN ALKADIENES...

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This reaction is forbidden. The symmetries of the orbitals are such that one interaction is bonding and the other is antibonding. The same answer is obtained if the HOMO of allyl cation and the LUMO of ethylene are examined. ( b ) In this part of the exercise we consider the LUMO of allyl cation and the HOMO of 1,3- butadiene. This reaction is allowed by the Woodward Hoffmann rules. Both interactions are bonding. The same prediction would be arrived at if the HOMO of allyl cation and LUMO of 1,3-buta- diene were the orbitals considered. 10.39 Since oxygen has two unpaired electrons, it can abstract a hydrogen atom from the allylic position of cyclohexene to give a free-radical intermediate. The cyclohexenyl radical is resonance-stabilized. It reacts further via the following two propagation
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