Chemistry of aromatic compounds
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Chemistry of Aromatic Compounds. Electrophilic Aromatic Substitution Directing Effects Side-chain Reactions Synthesis Nucleophilic Aromatic Substitution. Electrophilic Aromatic Substitution. EAS Reactions of Benzene. Bromination / Chlorination. Bromination Mechanism. Reaction Profile.

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Chemistry of aromatic compounds

Chemistry of Aromatic Compounds

Electrophilic Aromatic Substitution

Directing Effects

Side-chain Reactions

Synthesis

Nucleophilic Aromatic Substitution













1 st formaton of electrophile
1st, Formaton of Electrophile



Intermediate is resonance stabilized
Intermediate is Resonance-Stabilized



Friedel crafts alkylation many more limitations
Friedel-Crafts Alkylationmany more limitations






1 o rx typically undergoes shift
1o RX Typically Undergoes Shift


Side chain reactions
Side Chain Reactions

1) Reduction of Aromatic Ketones








Ortho para directing activating groups
ortho/para-Directing Activating Groups



Nitration affords ortho and para products
Nitration Affords ortho and paraProducts


Activating ortho para directors
Activating ortho/para directors



Meta directing deactivating groups
meta-Directing Deactivating Groups



Meta directors
meta Directors



More limitations with friedel crafts reactions
More Limitations with Friedel Crafts Reactions



Halogens are the anomoly deactivators and o p directors
Halogens are the AnomolyDeactivators and o,p-Directors


Reactions of rings with two or more substituents
Reactions of Rings With Two or More Substituents






Sulfonic acid blocks para position
Sulfonic Acid Blocks para Position








S n a criteria
“SNA” criteria:

  • Strongly deactivated ring

  • Leaving group

  • Deactivating group(s) ortho &/or para to leaving group (preferably)

  • Strong base (nucleophile) such as RO-, NH2-






Carbons are sp2 not a second p bond
Carbons are sp2 (not a second p bond)


Benzyne can be trapped by a diene undergoes a diels alder rxn
Benzyne can be trapped by a Diene:Undergoes a Diels-Alder rxn




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