PS6 - Honors Organic Chem Problem Set 5 Question 1 Due...

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Honors Organic Chem. Problem Set 5 Due April 4 th Question 1 O OH OH OH OH H H OH H OH H OH CH 2 OH H O O OH OH OH O H H OH H OH H OH CH 2 OH H O H OH H OH CH 2 OH H O H H O R R R Please bring your molecular models for the exam. D-aldopentose derived from D- glyceraldehyde D-Ribose β -anomer Hold constant Rotate shown 1. i and ii) for (a) H OH H OH CH 2 OH H O H OH C C H OH H OH CH 2 OH O OH H O H H OH H OH CH 2 OH H O O H H 1. iii) Epimerization under basic conditions Sugars that differ by the stereochemistry at a single carbon are called epimers. OH : .. .. .. : .. Stereochemistry at C2 carbon is lost upon enolate formation O CH 2 OMe OMe OMe OMe OMe R R' O R'' H H C H H I Ag O Ag R R' O R'' H CH 3 Reaction for any one of the 5 hydroxyls δ + δ + δ− : .. δ− δ + : + Overall Product The silver oxide polarizes the CH 3 -I bond making the methyl more electrophilic 1. iv)
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H OH H OH O H H H O CH 2 OH H OH O H O OH OH OH OH H H OH H OH OH H H O CH 2 OH H OH H OH H OH OH H H O O H CH 2 OH H O OH OH OH OH CH 2 OH O OH OH OH CH 2 OH
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