Problems_3rd_Review - CEM 252 Review Session #3 November...

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Unformatted text preview: CEM 252 Review Session #3 November 29, 2010 1. Draw the Ketone, Enol (kinetic) and Enolate (thermodynamic) of Z-methyl-B-pentanone (6131‘s, 2 p15 each box) ketone I Enol (kinetic) Enolate (thermodynamic) 2. Rank the following underlined p_Iotons in order of increasing acidity (decreasing 131(3) (6 pfs) O O O O O O 0 fl . H H U H A B C D E F mi i 1WD Increasing Acidity High pKa LOW pKa 3. Complete the following reactions: Hi0“ woe, Hi3 H _____. ll” ‘ H 1; NEHQDH MD H ma at: = H Hfi‘fififi‘l 3. 1WC§ éHEOH 4; HQE} HUI -» 1. Nail]. H1613 .GH 2. HQ.- ILitlthEr cat. a“ p 3. Haw 4. Determine the structure of the following compound based on the IHANMR spectrum given. Put. your final stmcture in the box (show work for partial credit). (6 pm) CSHBN 2 1 1 1 {Lt é; s 4 é—r—F—‘fi—ré PPM 1H-NMR: 0.91 ppm ((1, 6H); 1.12 ppm (d, 3H); 2.06 ppm (octet, 1H); 2.78 ppm (quintet, 1H); 5.11 ppm (broad singlet, 2H). 5 . Provide a detailed mechanism for the following Hansfomlation O 0 OH 1. NaOH ~———b~ 2. H+ . 6. Provide a reasonable synthesis for the following transformations: a. ' OH 0 o ' MOB —» b. 0 NH " ——>~ cl. 7. Provide the starting material, reaction conditions or products for the following reactions: OCH 3 1. NaOCH3 - 2. H3O+ NT‘ 9-8 I 0.") to O O O I (.0 1. CH3|32r (excess) NH2 2. A920, H20 3. heat 1. LDA t WO\ 2. PhSeCI O 3. H202 ’ t O O I + HV NaOH l O 1. HNOg, H2804 NH2 ‘ 2. KCN 3. CH3MgBr 4. Hso+ 0H 3. H3C)_+, heat was Mi 1.. NaN3 ' 0| 2. H-3O+, heat ...
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This note was uploaded on 01/23/2011 for the course CEM 252 taught by Professor Rathke during the Spring '08 term at Michigan State University.

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Problems_3rd_Review - CEM 252 Review Session #3 November...

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