11 - Chem 10172, Spring 2008 (1) OSO2CH3 PROBLEM SET 11...

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Chem 10172, Spring 2008 PROBLEM SET 11 SOLUTIONS Due Tuesday, April 15 1 (1) (i) Cl Cl OSO 2 CH 3 LiOCH 2 CH 3 THF Note the chemoselectivity (the chloride cannot do elimination because it has no β - hydrogens, it cannot do S N 1 since it would make a 1º carbocation, and S N 2 will be exceedingly slow since it is so hindered), the regioselectivty (the more substituted alkene is favored, Zaitsev’s rule), and the stereoselectivity (only the stereoisomer shown is possible in an anti-periplanar E2 reaction). (j) NaOMe, MeOH I Only the indicated compound can form by an anti-periplanar E2 elimination. (2) (a) HO OH O H OSO 3 H HO O H H CH 3 CH 3 HO CH 3 CH 3 O 1,2-shift H resonance H OSO 3 H O (b) The 1,2-shift makes a cation that is very strongly stabilized because of the second resonance structure, since it obeys the octet rule. (3) Cl Acetone/H 2 O OH + OH + Cl This is a poor example of an S N 1 reaction since that is a very minor component of the observed reaction. The major reaction would be E2, and to the extent that the
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This note was uploaded on 05/18/2008 for the course CHEM 10172 taught by Professor Brown during the Spring '08 term at Notre Dame.

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11 - Chem 10172, Spring 2008 (1) OSO2CH3 PROBLEM SET 11...

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