Solutions_Manual_for_Organic_Chemistry_6th_Ed 212

Solutions_Manual_for_Organic_Chemistry_6th_Ed 212 - 9 -36 e...

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Unformatted text preview: 9 -36 e limination on 3° halide (c) CH3CH2-C:::C - CH20H (after H20 workup) OH (e) CH3CH2 -C::: C - CHCH2CH2CH3 (after H20 workup) OH ( g) CH3CH2 - C::: C - C -CH2CH3 (after H20 workup) 9 -37 NaNH2 (a) (b) HC::C-H HC::C-H • I I I Na+ -0-0 C H3 HC::C: HC::C: --=----"'--..::.-.. .. . NaNH2 • CH3CH2CH2B r HC::C -CH2CH2CH3 NaNH2 ..f---. .. . -- CH3I � (c) H3C-C:: C - CH2CH2CH3 synthesized in part (b) H2 Lindlar catalys t Na • H3 C \ C=C I CH2CH2CH3 H H3C \ H I H CH2CH2CH3 (d) H3C -C:: C - CH2CH2CH3 synthesized in part (b) H I C=C \ (e) H3C-C:: C - CH2CH2CH3 synthesized in part (b) 2 equiv. H2 Pt 2HBr Br H3C -C -CH2CH2CH2CH3 Bf I I (f) HC = C- CH2CH2CH2CH3 synthesized in part (a) 2 05 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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