Solutions_Manual_for_Organic_Chemistry_6th_Ed 459

Solutions_Manual_for_Organic_Chemistry_6th_Ed 459 - 19-43...

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Unformatted text preview: 19-43 This fragmentation is favorable because the iminium ion produced is stabilized by resonance. Also, there are three possible cleavages that give the same ion. Both factors combine to make the cleavage facile, at the expense of the molecular ion. CH3 t? I CH3 -NH2 + . CH3 --- CH3 58 oCH3 + mass 15 ..f--l� .. ... - .. C = NH2 CH3 I I + mlz 73 19-44 mlz 58 (a) (b) 0 O �I �I Cl-C �-o .. NH2 + 1) LiAlH4 (e) (I) CN-CH3 C N-CH3 H202 .. H202 .. (g) CH3 Y'1( COOH SOCl2 /�o CN CH3 /o N� C CH3 .. .. ---- t:. ( oH N. "'CH3 o 454 ...
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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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