2008TEst1A_2204-6-8 - (’08 Test 1A Page 2 3c(8 Show the...

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Chemistry 2204/6/8 (’08) Test 1A Name: Marks are in parentheses 1 (3) For each of the molecules shown below, point out, with an arrow, the carbon bearing ketone or acetal functionality. 2a (6) Indicate, with an arrow, the most acidic sites on the following ketone/aldehyde. Draw the corresponding enol tautomer (s) of each ketone/aldehyde in each case. Calculate the degree of unsaturation for each aldehyde/ketone. O O H O H enol enol deg unsat = deg unsat = 2b (1) Rank the following 3 molecules with respect to oxidation level. (1) highest (3) lowest O O OH 3a (8) Show the reagents necessary for each reaction. O H H 3 CS SCH 3 O D D D D D D O H OH O O H O H O H OH + 2 HSCH 3 H2O H+ H2O H+H2O H+ H+ H+, heat 3b (8) Show the starting material which would lead to product. R-C(=O)OOH CH 3 I O OH O O O 1. NaH 2. 1.H 2 C=O, H + , 2. H 2 /Pt 1.NaBH 4 H H 2. H +
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Chemistry 2204/6/8
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Unformatted text preview: (’08) Test 1A Page 2. 3c (8) Show the expected product(s) for each of the following reaction O HO Br 2 , H + CrO 3 H+ O HO O NH 3 H + H + acyclic form 4a (6) MECHANISM: Draw a mechanism for the following reaction, showing all intermediates, all curly arrows describing electron movement and all charges (if applicable). N H H 2 O + H + H 2 N O H : 4b (6) Use the appropriate pKa equations to show why LDA (Li diisopropylamide, pKa diisopropylamine 35) can be used to quantitatively deprotonate a typical aldehyde (pKa 19). 5 (4) Synthesis. Show how aldol reactions can be used to synthesize the following α , β-unsaturated carbonyl-containing compounds. Show the intermediate aldol formed in each case. O O...
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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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2008TEst1A_2204-6-8 - (’08 Test 1A Page 2 3c(8 Show the...

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