This preview shows page 1. Sign up to view the full content.
Unformatted text preview: the greatest percentage of the conformer with the ethyl group axial; cross out the one which would have the lowest fraction of the conformer with the ethyl group axial. n-Bu H H Et H H Et sec-Bu Me H H Et (Et = ethyl; n-Bu = n-butyl; sec-Bu = sec-butyl; Me = methyl) Product 'X' had to come from the radical shown at the right: O H The carbon with the odd electron is electron deficient (only 7 outer shell electrons); it will be destabilized by bond polarization by the neighboring oxygen (electron withdrawal by induction), but will be stabilized by electron donation via delocalization of an oxygen lone pair in a neighboring orbital (electron donation by resonance) - since this radical must be preferred, the resonance effect must overwhelm the inductive effect....
View Full Document
- Fall '08