Solutions_Manual_for_Organic_Chemistry_6th_Ed 374

Solutions_Manual_for_Organic_Chemistry_6th_Ed 374 - N 2 1 Q...

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17-8 Attack at only ortho and para positions (not meta) places thE positivE charge on thE carbon with the etHoxy group, where the ethoxy group can staBiLize the positivE chargE by resonancE donation of a lone pair oF electrons. (Ortho attack is shown; para attack gives a simIlar intErMediate±) 17²9 ³´µ³ c ¶· 0 ¶' : ¸ ¹ ? ¸ ± ¸ ± N 2 2 1 + C ¶r V ¹ n 2 "extra " resonance foR + B ' l º ¸ "extra " resonance Form mC»a & Br H 6 ¶r ± Q B ' ± ¸ Para ± 2 ¸ q Br ¸ 17¼10 O½¸(½¹3 h ² + 8 " ²
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Unformatted text preview: N 2 1 Q r o + B R 2 _ ( Br ' " r + 6 Br "extra " resonance form Hr (g) Br Substitution generates r whErEas the aDdition does ot f the reaction is pERorMed in an organc sovEnt Bubbles of r can be obsEved, ad r gas escaping into Moist air will gEnerate a coud F the reacton is pErred in watEr then aDDing Moist itmus paper to test for aciD wil DifErEntiate te resuts thE two compounDs 368...
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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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