215F07-notes-9-21-07 - Chem 215 F07 Notes Dr Masato Koreeda...

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Chem 215 F07 Notes – Dr. Masato Koreeda - Page 1 of 4. Date: September 21, 2007 Chapter 13. Alcohols, Diols, and Ethers: V. Reactions of alcohols: Alcohols to alkyl halides VIII. Epoxides (or Oxiranes): b. Ring-opening reactions of epoxides: Epoxides are highly strained and easily undergo ring-opening reactions under both acidic and basic conditions. + Acidic conditions : ring-opening reactions proceed rapidly at low temperatures (usually at room temp or below); elongated C-O bonds of the protonated, highly strained epoxides believed to be the origin of high reactivity. H 3 C CH 3 O H H meso Br H 3 C CH 3 OH H H (2 S ,3 S ) (2 R ,3 R ) H 3 C CH 3 H H Br HO HBr 0 °C racemic mixture H Br H 3 C CH 3 O H H Br H Br H 3 C CH 3 O H H H Br S N 2- like inversion of stereochemistry here! S N 2- like inversion of stereochemistry here! O H CH 3 OH O H H O CH 3 O H H O CH 3 H O CH 3 or simply B O H O CH 3 A c y c l i c e p o x i d e s C y c l i c - f u s e d e p o x i d e s inversion of stereochemistry + enantiomer
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  • Fall '07
  • Koreeda
  • Reaction, Nucleophilic substitution, H3C H3C, H3C D3C, H3C D H3C

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