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Solutions_Manual_for_Organic_Chemistry_6th_Ed 467

Solutions_Manual_for_Organic_Chemistry_6th_Ed 467 - 19-55(a...

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19-55 ( a) F OZN 'Q oo I N H z R .. N02 0 0 0 + 0 0 -; + 0 + o li o F NH2R 0 1 o F N H z R II 1j F NH 2 R _ 0 0 N:" Y - 0 0 N + N + : 0 '" 'c 0 I :0 '" I - 0 '" I I .. . �.. 00 C- + + 1 + .. . N.. .. _ .. . N .. .. _ .. . N .. .. 0 0- 0'" 0 0 '" 0 :0'" 0: (b) Why is fluoride ion a good leaving group from A but not from B (either by SNI or SN2)? _ y F Nu N02 H C I A NO z A :NU C B Formation of the anionic sigma complex A is the rate-determining (slow) step in nucleophilic aromatic substitution. The loss of fluoride ion occurs in a subsequent fast step where the nature of the Jeaving group does not affect the overall reaction rate. In the SN 1 or SN2 mechanisms, however, the carbon-fluorine hond is breaking in the rate-determining step, so the poor leaving group ability of fluoride does indeed affect the
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