Chem210-1 F08 Ex1 p05a

Chem210-1 F08 Ex1 p05a - the greatest percentage of the...

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O O O H (question 5, continued) c) In the reaction described on the previous page, product 'X' on the right is formed in major preference to compound 'Y', also shown here. Rationalize that observation - be as specific as you can be as regards the intermediates involved, and why one would be favored relative to the other (5 points) = 'X' O O O H = 'Y' 6. Select the best answers according to the criteria specified (3 pts each, 18 pts total) a) Of the C 10 H 20 isomers shown below, circle the one which would give off the most heat on combustion; cross out the one which would give off the least. H H H H b) Of the C 5 H 6 O isomers below, circle the one which would have the most ring strain; cross out the one expected to have the least. C O H 3 C O C H O c) Of the 1,4-disubstituted cyclohexanes shown below, circle the one which would have
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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....
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