Solutions_Manual_for_Organic_Chemistry_6th_Ed 351

Solutions_Manual_for_Organic_Chemistry_6th_Ed 351 - 1 6- 1...

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Unformatted text preview: 1 6- 1 3 61t The reason r the dipole can gives in resonance fo charge and the other ring positive charge. electrons. This foresonance picturebe seenonearing a negativerm distributing the electronsa to give each ring aromatic 61t ( sdelocaJizing the forms everal resonance sdeveral resonance forms"\ elocalizing the negative ____ charge around the five­ positive charge around ___ the seven-membered membered ring nng "'---- ----� �--------�---------- tropylium electrons ion � aromatic 61t �--------� cycIopentadienyl anion electrons � �--------� composite resonance picture shows rings are aromatic with charge separationboth that 1 6- 1 4 + AgBF4 -- aromatic cyc\opropenium ion CI !KCI The crystalline material soluble / icnycIopropenium solvents polar organic tetrafluoroborate. Cl-<Jl carbon.Draw resonance forms showing the carbonyl polarization,leaving a positive charge on the carbonyl 0 0 0 is AgCl + 1 6- 1 5 & t 21t :0 : +CI B electronsAROMATIC 0 61t t. .0: :I 0 .t. :0: +CI electronsAROMATIC 41t 345 The three-and sevenmemberedthe fiveamembered rings romatic; ntiaromatic and, 0 asurprisingly,very reactive. electronsANTI AROMATIC are ring is nut ...
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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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