Chem 120 Reaction of Aromatic Hydrocarbons

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Chem 120 Reaction of Aromatic Hydrocarbons

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Presentation Transcript

Slide 1: 

Reactions of Aromatic Compounds

Slide 2: 

Amphetamine

Slide 3: 

Adrenaline

Slide 4: 

Bromination of Benzene Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation

Slide 5: 

Chlorination of Benzene

Slide 6: 

An Example of Chlorination of Benzene Diazepam is marketed as the antianxiety agent Valium

Slide 7: 

Iodination of Benzene

Slide 8: 

Example of Iodination of Benzene This is the reason for encouraged use of Iodized Salt

Slide 9: 

Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation Nitration

Slide 10: 

Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation Nitration Sulfonation

Slide 11: 

Example of Sulfonation Sulfanilamide, one of the first antibiotic

Slide 12: 

Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation Nitration Sulfonation Friedel-Crafts Alkylation

Slide 13: 

Practice on Friedel-Craft Alkylation

Slide 14: 

Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation Nitration Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation

Slide 15: 

Summary of Electrophilic Aromatic Substitution Reactions

Slide 16: 

Activating Substituents increase the speed of the reaction Deactivating Substituents decrease the speed of the reaction Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation Nitration Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Effects of Substituents on Rates of Reaction

Slide 17: 

Some substituents direct the substitution to the ortho and para positions. Methyl (-CH3) is an Ortho, Para Directing Substituent Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation Nitration Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Effects of Substituents on Rates of Reaction Ortho, Para, and Meta Directing Substituents

Slide 18: 

Pero some substituents direct the substitution to the meta position Trifluoromethyl (-CF3)is a Meta Directing Subtituent

Slide 19: 

List of Substituents Based on their Effect on Orientation of Substitution and Rates of Reaction

Slide 21: 

Practice on Ortho, Meta, Para Directing Substituents

Slide 22: 

Practice on Ortho, Para, and Meta Directing Substituents

Slide 23: 

Practice on Ortho, Para, and Meta Directing Substituents

Slide 24: 

Practice on Ortho, Para, and Meta Directing Substituents

Slide 25: 

Let’s look at the effects of a methyl and nitro substituent Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation Nitration Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Effects of Substituents on Rates of Reaction Ortho, Para, and Meta Directing Substituents Effects of Polysubstituted Aromatic Compounds

Slide 26: 

If the directing effects of the two groups oppose each other, the more powerful activating group has the dominant influence

Slide 27: 

Substitution rarely occurs between the two groups in a metadisubstituted compound because this site is too hindered (stearic effect)

Slide 28: 

Practice on Ortho, Para, and Meta Directing Substituents

Slide 29: 

Practice on Ortho, Para, and Meta Directing Substituents

Slide 30: 

Practice on Ortho, Meta, Para Directing Substituents

Slide 31: 

Practice on Ortho, Para, and Meta Directing Substituents

Slide 32: 

Practice on Predicting the Product of Substitution on a Polysubstituted Benzene

Slide 33: 

Practice on Predicting the Product of Substitution on a Polysubstituted Benzene

Slide 34: 

Practice on Predicting the Product of Substitution on a Polysubstituted Benzene

Slide 35: 

Reactions of Aromatic Hydrocarbons Electrophilic Aromatic Substitutions (EAS) Halogenation Nitration Sulfonation Friedel-Crafts Alkylation Friedel-Crafts Acylation Effects of Substituents on Rates of Reaction Ortho, Para, and Meta Directing Substituents Effects of Polysubstituted Aromatic Compounds