Solutions_Manual_for_Organic_Chemistry_6th_Ed 180

Solutions_Manual_for_Organic_Chemistry_6th_Ed 180 - 8-40...

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Unformatted text preview: 8-40 H-B is used here to symbolize a generic acid. :B - alkenes p olymers (colored) � � Note : the dashed bond symbol is used here to i ndicate the continuation of a polymer chai n . 8-41 I -----I H H C-C · Ph I H + H I� n/) \ � \...( H \ C =C / H H ------ CC-C- · C 10 radi cal , and not resonance-stabilized­ this orientation is not observed I H H I Ph I I H Ph I I H I H I O rientation of addition always generates the more stable intermediate; the energy difference between a 10 radical (shown above) and a benzylic radical is huge. The phenyl substituents must necessarily be on alternating carbons because the orientation of attack is always the same-not a random process. 8-42 F or clarity, the new bonds formed in this mechanism are shown in bold . RO - OR H RO · + 2 R O· .!) � � \...( \H \ C =C / H ---t.� H R O-C-C. H I I H C C �'""+-",,/ V \ o, I( H H H \ / H H .. H I R O-C-C-C-C · H I H I I H H I I H H I H etc. ---- R O-C-C-C-C-C-C· I H H 173 I I H H I I H H I I H H I I H I \c/ l H k) ) \H I / H I H I ...
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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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