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Solutions_Manual_for_Organic_Chemistry_6th_Ed 374

Solutions_Manual_for_Organic_Chemistry_6th_Ed 374 - ¹ N 2...

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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: ¹ N 2 ³ 1 ½ Q ¶r ¸ o + B R 2 _² ( Br ' " ¶r ¹ ¹ + 6 Br ¹ "extra " resonance form ´ Hr (g) ¢ ¹ Br ¸ Substitution generates ¾r whErEas the aDdition does ¿otÀ Áf the reaction is pERorMed in an organÂc soÃvEntÄ Bubbles of År can be obsEÆved, a¿d Çr gas escaping into Moist air will gEnerate a cÃoud± ÈF the reactÉon is pErÊrËed in watErÄ then aDDing Moist Ãitmus paper to test for aciD wiÃl DiÌfErEntiate tÍe resuÃts ÎÏ thE two compounDsÐ 368...
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