2009 TEst2A2204-6-8 answers - 2204/6/8 (08) Test 1A Page 2....

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Chemistry 2204/6/8 (’09) Test 2A Name: Marks are in parentheses 1 .(17) Name the top 10 reactions of the carboxylic acid family and give an example of each using prototypical compounds and reagents. Note: 3 reactions are subdivided into subcategories. See notes 2 .(4) For each of the molecules shown below, circle and name at least 2 functional groups. Carboxylic acid Amide ester carboxylic acid O H N H O O O OMe H H N H 2 ester amine 3a (4) Indicate, with an arrow, the most acidic site(s) on the ester shown below. Draw the enol tautomer of the ester . Calculate the degree of unsaturation of the parent ester – show the details of your calculation. O O enol deg unsat = OH O 2 (4x 2) + 2 ( ) - 8 = 1 3b (1) Rank the following 3 molecules with respect to oxidation state. (1) highest (3) lowest OH O O H O H O H OH 2 1 3 4a (2) Name the following molecule. O Cl 2E-pentenoyl chloride 4b (2) Draw the correct structure for the following sixteen carbon molecule. Show stereochemical details. ( S )- 10-hydroxy-7Z-hexadecenoic acid: O OH OH 7 10 Chemistry
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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.

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2009 TEst2A2204-6-8 answers - 2204/6/8 (08) Test 1A Page 2....

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