Solutions_Manual_for_Organic_Chemistry_6th_Ed 450

Solutions_Manual_for_Organic_Chemistry_6th_Ed 450 - 19-22...

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Unformatted text preview: 19-22 continued (b) Hofmann elimination (CH3) 3N+ \� ,) "C H H3C "I --- "-\ - 5=H(CH3h f�CH3 C HO: H� .. ",CH(CH3h 'I, IIC::::: C" � "' H3C CH3 " ,,\ H (Saytzeff product-more highly substituted) E Cope elimination .. 19-23 ",CH3 IIC-C" � - "' H3C CH(CH3h H" '1 / ,\\ (Saytzeff product-more highly substituted) Z + Aliphatic diazonium ions are very unstable, rapidly decomposing to carbocations. (b) /' " NO N o (d) � (c) NO 19-24 The diazonium ion can do aromatic substitution like any other electrophile. o I 6 H I+ _ N2 + ClAryl diazomum IOns are relatively stable If kept cold. i 03S � � � --- -03S -o- N=NV-o- N=N N(CH3h �(CH3h � HO . . .. plus two other resonance forms most slgmflcant resonance contnbutor .. with positive charge on the ring .. :Cl: _ - 03S -< >- N N -< >- N(CH3h = j � _ (or some other base) } methyl orange 445 ...
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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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