Chapter14 - Chapter 14 Br Bensene ; C 6H6 C6H5Y 1 isomer Br...

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Chapter 14 Bensene ; C 6 H 6 C 6 H 5 Y 1 isomer C 6 H 4 XY 3 isomer Br Br Br Br H hydrogenation , H comb for Benzene are lower than expected (~ 36 kcal/mole) Fig 14.1 substitution rxn rather than addition rxn (Table on p497) C C C C ; 1.34 A ; 1.53 A ; 1.50 A ; 1.48 A ; 1.39 A in CH 3 - CH 3 in CH 3 CH=CH 2 in CH 2 =CH - CH=CH 2 all in benzene C C hybrid of resonance energy = 36 kcal/mol substitution rather than addition to retain the ring system aromatic properties H sp 2 - s σ bond sp 2 - sp 2 σ bond 6 π eletrons are delocalized. π electrons are loosely held electrophilic substitution
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aromatic character ? a high degree of unsaturation electrophilic sybstitution rxn insted of addition rxn. low H hydrogenation , low H comb cyclic, flat. experimentally theorerically cyclic clouds of delocalized p electrons above and below the molecular plane (4n + 2) π electrons 4n + 2 rule or Huckel rule ex) benzene 6 π electrons (aromatic sextet) I II III IV
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Chapter14 - Chapter 14 Br Bensene ; C 6H6 C6H5Y 1 isomer Br...

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