2008TEst1A_2204-6-8 answer - Draw a mechanism for the...

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Chemistry 2204/6/8 (’08) Test 1A Name: 1 (3) For each of the molecules shown below, point out, with an arrow, the carbon bearing ketone or acetal functionality. Acetal acetal ketone 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 OH H O H OH deg unsat = 5 deg unsat = 2 2b (1) Rank the following 3 molecules with respect to oxidation level. (1) highest (3) lowest O O OH 1 2 3 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 + O O O H O
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Chemistry 2204/6/8 (’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 OH O O O Br NH 4a (6) MECHANISM: Draw a mechanism for the following reaction, showing all intermediates,
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Unformatted text preview: 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 : HN H HN H OH 2 H 2 N H OH H 2 N HO 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). DiisopropylAmine + H 2 O = Diisopropylamide + H 3 O + K = 10 -35 eqn1 Aldehyde + H 2 O = enolate + H 3 O + K = 10 -19 eqn 2 Add eqn 2 + reverse of eqn1: Diisopropylamide + Aldehyde = Enolate + DiisopropylAmine K= 10 +35 x 10-19 = 10 16 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 O O O HO via O O via O OH...
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  • Winter '08
  • Dr.Levin
  • Carbonyl, Keto-enol tautomerism, corresponding enol tautomer, Li diisopropylamide, H2O H+H2O H+H, following reaction Br

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