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


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