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carbo key - Carbohydrates Problem Set Winter 2010 Answers 1...

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Carbohydrates Problem Set – Winter 2010 Answers 1. Complete the Fischer projection and/or chair conformation templates of the three sugar compounds below. 2. When β -D-galactose is dissolved in water it has an initial optical rotation of + 52.8° which slowly increases to + 80.2°. Using all significant chemical structures and a few brief sentences, explain what is occurring. In water, beta D-galactose undergoes mutarotation (equilibrium between open chain carbonyl form and ring hemiacetal form). The mixture of alpha and beta has a different optical rotation than pure beta form (alpha and beta anomers are diastereomers and it is not possible to predict the specific rotation of one from the other). O OH H H HO OH OH H H H OH H HO H HO CHO H HO CH 2 OH OH H i) OH H H HO CHO OH H CH 2 OH H HO O H HO OH H H OH OH CH 2 OH H H ii) H HO OH H CH 2 OH O CH 2 OH OH H O H HO OH H OH OH H H H CH 2 OH iii) beta pyranose form alpha pyranose form O OH H H HO H H OH H OH OH beta D-galactose OH OH H H HO H H OH H O OH O OH H H HO H OH OH H H OH alpha D-galactose
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3. Provide the structure(s) of the major organic product(s) obtained from each reaction.
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