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Unformatted text preview: z- 326 students What is this? Friday, March 7, 14 9 Prelecture Quiz- 326 students ? CH3 A O CH3 O H 3C O O B O Friday, March 7, 14 H 3C O O C O D O O O O 10 Drill O O NH 2 A H + /H2O ? SOCl2 Cl Such is the transformation O H + /H2O NH 2 B P 4O10 SOCl2 C SOCl2 D SOCl2 OH O Cl H + /H2O H + /H2O O HCl Friday, March 7, 14 11 Drill Which is the plausible 2nd intermediate of this mechanism? H O O O H H3O O O H H O + H O O O OH O H H O O O OH OH HO H O A O O O H O B O O O H O H O H H O O O H H C O O O O This is the first i ntermediate OH H H O O O H H D HO H O O O O H O H O O O OH H H H O H O O H O I made a mistake here This never happens H H O H O O O OH H O H H OH OH H O O O H H O O O H Great mechanism question: poor answer choices -->my fault Friday, March 7, 14 12 Drill O O OH O 1 O 2 O O 1 A HO O 2. H 2O 1. NaBH 4 1. LAH 2. H 2O H 3O+ H+ H 3O+ 2. H 2O OH HO Friday, March 7, 14 O H+ 2. H 2O O No need for this after LAH 3 H 3O+ 2. H 2O OH HO O 3 This is the right choice, but there is a reagent that is used redundantly OH 2 1. LAH 1. NaBH 4 1. LAH C D O H+ B OH HO Hot Conc. KMnO 4 1. NaBH 4 2. H 2O OH H+ 1. NaBH 4 H 3O+ 2. H 2O 13 Drill Which of the following is a plausible intermediate for the transformation depicted? PPh3 1) O O MeO H 1 2) H3O+ O A PPh 3 C H O C Friday, March 7, 14 PPh 3 O C H H I changed the c hoices for them to make sense PPh 3 C O H H 3C H 3C O O B O C H O D PHPh 3 C H H PPh 3 O CH3 This was choice ‘C’ which was a lso an i ntermediate of t his rxnI apologize to 322 students O H 3C 14 O O N EtO O O OEt 1 OH O ) OEt OO ? O O Happy Robot OH 3 EtO Br O 2 (f) O Drill OH 2 1 3 .42 Using any compounds of your AH choosing, H O+ a method for preparing each of identify 1. L HO 3 e following compounds. Your only limitation is that the compounds you use can have no H + atoms. For purposes of counting carbon atoms, you may ignore the 2. H 2O re than two carbon enyl groups of a Wittig reagent. ThatOH you are permitted to use Wittig reagents. is, 1. LAH H 3O+ HO A B N NH HO C OH (b) H+ HO D N OH HO Friday, March 7, 14 H+ (f) O 2. HO 2O H+ H 3O+ 1. NaBH 4 (c) 2. H 2O OH H2N HO (g) O (d) OH H 3O+ 1. DIBALH 2. H 2O O (h) 15...
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This note was uploaded on 04/01/2014 for the course BIO 310 taught by Professor Lyman during the Spring '08 term at SUNY Stony Brook.

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