Lecture08outline

Lecture08outline - I Review A desirable method for...

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I. Review • A desirable method for carbon–carbon bond formation through EAS would provide products that are less reactive than the starting material by introducing an electron withdrawing group • Ketones can be formed by reacting arenes with acylium ions (RCO + ) in a process called Friedel-Crafts acylation • Acylium ions are formed from acid chlorides (or related species) in the presence of AlCl 3 and do not rearrange because they are fairly stable due to lone pair delocalization and because the rearrangement products are destabilized by the carbonyl group • The ketones formed from acylation reactions can be converted into several different functional groups (see Chem 0310) • Aromatic ketones can be converted to alkyl groups with H 2 NNH 2 and KOH (Wolff- Kischner reduction) or with Zn and HOAc (Clemmenson reduction), providing a two step sequence for accomplishing the equivalent of a Friedel-Crafts alkylation reaction with a primary carbocation • Metal groups can be added to benzene rings through EAS by using an electrophilic
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Lecture08outline - I Review A desirable method for...

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