Solutions_Manual_for_Organic_Chemistry_6th_Ed 479

Solutions_Manual_for_Organic_Chemistry_6th_Ed 479 - 20-10...

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Unformatted text preview: 20-10 conc. (a) �C C� or 1 ) 0KMn0420 �COOH 3, 2) H C-:::) conc. KMnO� C:COOH COOH H 0+ CH CH2CH20HH 04 62COOH (c ) < }- Br etMger < }- MgBr D H30+ 6 2Cr h (d) � PB r3 � Br Mg CO2 H30+ COOH � ether COOH (e) conc. KMn04 t"H30+ CH3 COOH Mger CO2 H30+ �COOH eth OR KCN �CN H30+ �COOH 20-11 • McLafferty rearrangement H3C I1�H� : �ft''OH C CH3 m/z1l6 t, , 3 [ CH3CH2tCH' H0-OH ] 87 CH3 m/z1l6 ig t t - -- :OH CH3asCs H,· H2C==C/C,9,..H m CH3 forms paslushown in 20-9 s resonance m/z 87 H,0..: H3C,CH ,/. CH2 HC/'C,OH mass 42 CH3 29 + + I \ t II + I I mlz74 (h) o -­ � --- � I • � I � -- --- � ( f) Q • �I -- --- ¢ • �I • t, 474 • ...
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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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