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Sample TEst2 2204-6-8 (4)

Sample TEst2 2204-6-8 (4) - 2204/6/8(2010 Sample Test 2A...

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Chemistry 2204/6/8 Sample Test 2 Name: Marks are in parentheses 1. (8) Circle and name any 8 functional groups found in the molecules shown below: 2a (4) Draw the enolate of the lactone (cyclic ester) shown below. Show the two resonance forms of the enolate. Calculate the degree of unsaturation of the parent ester – show the details of your calculation. O O enolate deg of unsaturation = Base enolate 2b (2) Rank the following 3 molecules with respect to oxidation state. (1) highest (3) lowest H O O OH O H O HO HO OH 3a (2) Name the following molecule. O OCH 2 CH 3 3b (2) Draw the correct structure for the following molecule. Show stereochemical details. Methyl ( S )- 12-fluoro-9Z-octadecenoate: 4a (8) Show the reagents necessary for each reaction. O O - K + O OH O OCH 3 O Cl O OH O Cl O NH 2 OH CH 3 OH HCl + pyridinium hydrochloride 1
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Unformatted text preview: 2204/6/8 (2010) Sample Test 2A Page 2/2 4b (8) Show the starting material which would lead to product. OEt O O NH 2 O O H+ + H 2 O NH 3 OAc-LiAlH 4 NH 2-OEt O-OEt 4c (8) Show the expected product(s) for each of the following reaction C N O Cl O O-O OMe H+, H 2 O EtO O OEt H + , H 2 O O heat + + + NH 4 LiAlH 4 1. 2. H+ workup 5 (6) MECHANISM: Draw a mechanism for the following reaction, showing all intermediates, all curly arrows describing electron movement and all charges (if applicable). N C O H 2 O + H + H 2 N O OH + 6 (2) SYNTHESIS: Show how you would synthesize the target molecules by showing the intermediate in each case. O OEt from Br O OEt from O O OEt O OH O OEt O O TARGET TARGET 2 3...
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