7_PAH_Hetaroaromatic_Substitution

7_PAH_Hetaroaromatic_Substitution - Chem 267 Basic Organic...

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Prof. Dr. Xiangdong Fang University of Waterloo Chem 267 Basic Organic Chemistry II 1
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Polycyclic Benzenoid Hydrocabons “the electron density in polycyclic benzenoid hydrocarbons is unequally distributed in the ring system” 2
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3 Clar’s Model of Aromaticity 1) each carbon atom has one 2p orbital with a single electron ( a dot to represent); 2) those electrons interact to form conjugated π orbital overlap; 3) the most stable system will be the one with maximum number of rings consisting of six π -electrons, i.e. benzenoid sixtets;
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4 pyrene triphenylene three benzoid sixtets very stable two benzoid sixtets double bond character single bond character
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5 Reactivity of Polycyclic Aromatic Hydrocarbons “use Clar’s Model to predict the reactive sites”
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6 O 9 10 Clar's model A B C A B C B both A and Cr ingsare benzenoid ( more stable ) KMnO 4 OH - O A B C H OMnO 3 possible radical intermediate Clar's model Br 2 two benzenoid rings very stable
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7 Clar's model Br 2 CCl 4 H Br H Br CrO 3 H + CO 2 H CO 2 H behave like a double bond
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This note was uploaded on 07/07/2010 for the course CHEM 267 taught by Professor Fang during the Winter '09 term at Waterloo.

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7_PAH_Hetaroaromatic_Substitution - Chem 267 Basic Organic...

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