2009 Template TEst2A_2204-6-8 - the following eighteen...

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Chemistry 2204/6/8 (’09) Template 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. 2 .(4) For each of the molecules shown below, circle and name at least 2 functional groups. 3a (4) Indicate, with an arrow, the most acidic site(s) on the ester shown below. Draw the corresponding deprotonated form . Calculate the degree of unsaturation of the parent ester – show the details of your calculation. O O enolate deg unsat = 3b (1) Rank the following 3 molecules with respect to oxidation state. (1) highest (3) lowest OH O O H 4a (2) Name the following molecule. O OCH 2 CH 3 4b (2) Draw the correct structure for
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Unformatted text preview: the following eighteen carbon molecule. Show stereochemical details. ( R )-12-hydroxy-9(Z)-octadecenoic acid: 1 Chemistry 2204/6/8 (’08) Test 1A Page 2. 5 (10) Supply the missing reagent, starting material or product for each of the following reaction. O O H HO H 1.LiAlH 4 O O H + CH 3-MgBr (2equiv) H 3 C O N R R + HCl O-OEt H 2 O + 1 2 H+ 2. H+ O Cl + R 2 NH OEt 2 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 MeO H 2 O + H + O HO : + MeOH 7 (5) SYNTHESIS: Supply the missing intermediates (2) and names of reaction types (3) in the last step of raspberry ketone biosynthesis. 2...
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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 Template TEst2A_2204-6-8 - the following eighteen...

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