Lecture2 - 282 Delocalized Electrons Dienes and Their...

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282 Lecture 2 – September 9 th , 2011 Delocalized Electrons Dienes and Their Reactions
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2 Localized / Delocalized Electrons v localized electrons belong to a single atom or are confined to a bond between two atoms H 3 C NH 2 localized electrons H 2 C H C CH 2 localized electrons v delocalized electrons are shared by three or more atoms H 3 C C O O H 3 C C O O H 3 C C O O δ - δ - delocalized electrons resonance structure or contributor resonance hybrid
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3 How to Draw Resonance Structures v Rules v only electrons move, never atoms v only π electrons and lone-pair electrons can move, never σ electrons v the total number of electrons in the molecule does not change CH 3 CH 2 N O O nitroethane CH 3 CH 2 N O O resonance contributors CH 3 CH 2 N O O δ - δ - resonance hybrid H 2 C H C H 2 C H C CH 3 an sp 3 carbon cannot accept electrons CH 3 CH C CH CH 3 CH C CH correct incorrect
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4 Resonance and Stability v Resonance structures do not necessarily contribute equally to the resonance hybrid v
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Lecture2 - 282 Delocalized Electrons Dienes and Their...

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