HT3-04 - H our Examination #3, Chemistry 302/302A - 2004 If...

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Hour Examination #3, Chemistry 302/302A - 2004 “If you are obliged to neglect any thing, let it be your chemistry. It is the least useful and the least amusing to a country gentleman of all the ordinary branches of science.” Thomas Jefferson 1 (21 points). Devise three different ways to convert methyl propionate into ketone 1 . You may also use isopropyllithium, pyridine, any one-carbon-containing compound, and the DNA from the last rancid yak of Tibet. Need something else? Ask us. Mechanisms are not necessary. What does “different” mean? The judges’ decision is final, but here are three hints: a. acetoacetic ester b. grind it out c. two equivalents of RLi OCH 3 O O 1 methyl propionate 2 (19 points). Aldohexose 2 was known to be either D-Glucose, D-Mannose, or D-Galactose. OH CHO H HO H OH H OH H CH 2 OH OH CHO H HO H H HO OH H CH 2 OH H CHO H HO HO OH H OH H CH 2 OH D-Glucose D-Galactose D-Mannose Reduction with sodium borohydride gives the corresponding D-hexa-alcohol 3 , which
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This note was uploaded on 03/07/2010 for the course ORGO 1 AND V.0243 taught by Professor Jones during the Spring '10 term at NYU.

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HT3-04 - H our Examination #3, Chemistry 302/302A - 2004 If...

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