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Unformatted text preview: 2204/6/8 (08) Test 1A Page 2. 5 (10) Supply the missing reagent, starting material or product for each of the following reaction. 1 H HO CH 3 1. 2 CH 3 MgBr O O H + H 3 C O-OEt H 2 O + 2. H+ O OH + R 2 NH OEt 2 + MeOH Hint : it's a salt 1. 2. H+ NH 2 HO H N HO O + O OH + spontaneous O O O H O OMe OH O HO O O-R 2 NH 2 O O OEt 6 (5) MECHANISM: Draw a mechanism for the following reaction, showing all 4 intermediates, all curly arrows describing electron movement and all charges (if applicable). Hint: PATLD! O O MeOH + H + O OCH 3 : OH O O HO O HO OH HO OCH 3 OH OMe H OMe H P A T L D 7 (5) SYNTHESIS: Supply the missing intermediates (2) and reaction types (3) in the last steps of raspberry ketone biosynthesis. O HO O SCoA HO O SCoA Claisen hydrolysis decarboxylation O HO + + CO 2 reduction O HO O OH O HO Bonus: Draw the mechanism of acid chloride formation using oxalyl chloride as the chloride source. 2 3...
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This note was uploaded on 07/28/2009 for the course ORGANIC CH CHEM 2204 taught by Professor Dr.levin during the Winter '08 term at Indian Institute of Technology, Chennai.
- Winter '08