Tsantrizos-Lectrure%207-Aromatic%20Chemistry-Part%20B

Tsantrizos-Lectrure%207-Aromatic%20Chemistry-Part%20B -...

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Unformatted text preview: ORGANIC CHEMISTRY 211 / 212 TSANTRIZOS - Lecture 7 romatic Chemistry romatic Chemistry art B art B Aromatic Chemistry Aromatic Chemistry Part B Part B November 9 th , 2010 ORGANIC CHEMISTRY 212 Chapters 14 and 15: AROMATIC COMPOUNDS- Properties- History- Names- Reactions Relative Heat of Hydrogenation E N T H A Expected value for a triene ~ -360 kJ/mol L P Y H o = -120 kJ/mol H o = -232 kJ/mol H o = -208 kJ/mol product Benzene H H H H H H H H H H H H Best representation of the correct structure - - + + Reactions of Aromatic Compounds H H H H H AlCl 3 CH 3 CH 2 Cl CH 2 CH 3 H H H H H Cl H H H H H Cl 2 FeCl 3 NO REACTION Cl 2 H Electrophilic Aromatic Substitution Br 2 Substitution FeBr 3 Br 2 Addition Electrophilic Aromatic Substitution E- X E = electrophile X- = derived anion E H + + + X - Electrophilic Aromatic Substitution E-X Substitution E H Arenium ion reaction intermediate + + + + Slow rate determining step Fast step Re-aromatization! Electrophilic Aromatic Substitution Br 2 Substitution FeBr 3 + Reactions of Aromatic Compounds FeBr 3 Br 2 Br Br FeBr 3 +- Br H + Br H + +- Reactions of Aromatic Compounds FeBr 3 Br 2 Br Br FeBr 3 +- +- Br HBr Friedel-Crafts Alkylation Reaction...
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This note was uploaded on 11/15/2010 for the course CHEM 212 taught by Professor Harpp during the Spring '08 term at McGill.

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Tsantrizos-Lectrure%207-Aromatic%20Chemistry-Part%20B -...

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