Week 7 Objectives - Describe the aspects of Friedel-Crafts...

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Page 1 of 1 Weeks 1-2: Reactions of Benzene and its Derivatives: electrophilic aromatic substitution, chlorination, bromination, nitration, sulfonation, Friedel-Crafts alkylation, Friedel-Crafts acylation, acylium ion, polysubstituted rings, ortho/para and meta directing groups, activating and deactivating groups, Objectives: Draw the general mechanism for electrophilic aromatic substitution of a benzene ring. Compare the products of bromination or chlorination of a benzene ring with the products of bromination or chlorination of an alkene. Describe the reason for the observed difference from the perspective of relative energies of the products. Draw the mechanism of nitronium formation, followed by reaction with a benzene ring. In Friedel-Crafts alkylation, draw the mechanism of alkyl cation formation and its reaction with a benzene ring.
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Unformatted text preview: Describe the aspects of Friedel-Crafts alkylation that limit its utility. In Friedel-Crafts acylation, draw the mechanism of acylium ion formation and its reaction with a benzene ring. Describe the advantages of Friedel-Crafts acylation over alkylation. Identify whether a substituent is ortho/para or meta directing and whether it is activating or deactivating. Using the directing effects of the substituents on a benzene ring, draw the products of electrophilic aromatic substitution of the ring. In a multi-step synthesis, show how the order of reactions can make a difference in the product observed. Use resonance structures of the cation intermediate to explain the basis for ortho/para and meta directing effects. Describe the basis for activating vs. deactivating effects....
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This note was uploaded on 01/22/2012 for the course CHEM II taught by Professor G during the Fall '11 term at University of California, Berkeley.

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