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Unformatted text preview: I. Review Benzylic substituents are those groups that are appended to carbons that are bonded to aromatic rings Reactive intermediates at benzylic positions are substantially stabilized through delocalization into the aromatic ring in a manner that is similar to allylic stabilization Benzylic positions react similarly to allylic positions, though additional reactions are possible because of the stability of the aromatic ring The weak benzylic CH bonds and the stability of benzyl radicals allows for selective benzylic halogenation by NBS and light Benzylic oxidation with KMnO 4 converts alkylbenzenes into benzoic acids Similar allylic oxidation is not possible because alkenes would be destroyed by KMnO 4 The easy conversion of alkylbenzenes to carboxylic acids is used in the body to convert alkylbenzenes into polar, water-soluble compounds that can be excreted As a consequence, alkylbenzenes aren't highly toxic but benzene, which is much more difficult...
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This note was uploaded on 05/17/2010 for the course CHEM 0740 taught by Professor Professor during the Spring '10 term at Pittsburgh.
- Spring '10
- Organic chemistry