Sample TEst 1A_2204-6-81 (1)

Sample TEst 1A_2204-6-81 (1) - HO HO O H+ O O NH 2 OH H +...

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Chemistry 2204/6/8 Sample Test 1 Name: Marks are in parentheses 1 (3) For each of the molecules shown below, point out, with an arrow , the carbons bearing the acetal functionality. 2a (6) Draw the corresponding enol tautomer (s) of each ketone/aldehyde in each case. Name the ketone/aldehyde in each case O O enol enol F F H 2b (1) Rank the following 3 molecules with respect to oxidation level. (1) highest (3) lowest HO O 3a (8) Show the reagents necessary for each reaction. O H HO CN O O H OH H 2 C O H H 3 CO H O H OH O ALDOL reaction 3b (8) Show the starting material which would lead to product. R-C(=O)OOH H+ O O O O 6Cl 2 H + , 1.NaBH 4 2. H + + H 2 O OH Cl Cl Cl Cl Cl Cl
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Chemistry 2204/6/8 Sample Test 1 Page 2. 3c (8) Show the expected product(s) for each of the following reaction
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Unformatted text preview: HO HO O H+ O O NH 2 OH H + 1. NaH HO H + O HO + H 2 O diketo tautomer 2. CH 3 CH 2 I 4a (6) MECHANISM: Draw a mechanism for the following reaction, showing all intermediates, all curly arrows describing electron movement and all charges (if applicable). O H NH 3 + H + H 2 O HN H 4b (6) Use the appropriate pKa equations to show why - OH (pKa H 2 O 15.7) cannot be used to quantitatively deprotonate acetone CH 3 C(=O )CH 3 (pKa 20). 5 (4) Synthesis. Show how aldol reactions can be used to synthesize the following , -unsaturated carbonyl-containing compounds. Show the intermediate aldol formed in each case. O O...
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Sample TEst 1A_2204-6-81 (1) - HO HO O H+ O O NH 2 OH H +...

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