HT3-04ans - Answers to Hour Examination#3 Chemistry 302/302A 2004 1(a 1 CH3 OH/CH 3 O 2 CH3 I 3 H3O heat(b 1 H3O/H2 O 2.2 Eq(CH3)2 CHLi 3 H2O 1 2 3

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Answers to Hour Examination #3, Chemistry 302/302A - 2004 1. 1. CH 3 OH/CH 3 O 2. CH 3 I 3. H 3 O + , heat (a) (b) 1. H 3 O + /H 2 O 2.2 Eq. (CH 3 ) 2 CHLi 3. H 2 O (c) 1. LiAlH 4 2. H 2 O 3. CrO 3 /pyridine 4. 1. (CH 3 ) 2 CHLi, 2. H 2 O 5. KMnO 4 2. The borohydride reduction leads to the following three possibilities for 3 . OH CH 2 OH H HO H OH H OH H CH 2 OH OH CH 2 OH H HO H H HO OH H CH 2 OH H CH 2 OH H HO HO OH H OH H CH 2 OH The corresponding hexa-acetates are A, B, and C: OAc OAc H OAc H CH 2 OAc CH 2 OAc H AcO H OAc CH 2 OAc H AcO H H AcO OAc H CH 2 OAc H CH 2 OAc H AcO AcO OAc H OAc H CH 2 OAc A B C Acetate C is optically inactive and is eliminated. Acetate B has three different methyl groups but acetate A has six!. The hexa-acetate is B, and the starting sugar must be D- D-mannose.
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3. The aldol condensation of acetone is endothermic. It will surely take place, but monomeric acetone is always the major compound in equilibrium with the aldol product, and thus is available for the crossed Claisen. The Claisen condensation of
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This note was uploaded on 10/13/2010 for the course CHEMISTRY V25.0243 taught by Professor Jones during the Spring '10 term at NYU.

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HT3-04ans - Answers to Hour Examination#3 Chemistry 302/302A 2004 1(a 1 CH3 OH/CH 3 O 2 CH3 I 3 H3O heat(b 1 H3O/H2 O 2.2 Eq(CH3)2 CHLi 3 H2O 1 2 3

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