L_14_09 - 318N Krische Lecture 14 Th Ch 22 We begin this...

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318N – Krische, Lecture 14: Th - 03/5/09, Ch. 22 We begin this lecture by discussing reactions of “extra-nuclear” substituents of aromatic compounds. Reactivity - Oxidation of the benzylic position : Exposure of alkyl-substituted benzenes to chromic acid (generated from K 2 Cr 2 O 7 and H 2 SO 4 ) yields benzoic acids. For example, toluene (a.k.a. methyl benzene) is oxidized to benzoic acid under these conditions. Remarkably, isopropyl benzene is also oxidized to benzoic acid under these conditions. However, tert -butyl benzene does NOT oxidize under these conditions, thus indicating that at least one benzylic hydrogen is required for this reaction. You should know this reaction, but are not responsible for the mechanism. Just as alkenes are subject to bromination of the allylic position, benzenes and other arenes are subject to bromination of the benzylic position. In class, we discussed the mechanism. SEE ONLINE HANDOUT FOR MECHANISM. Benzylic halides are excellent electrophilic partners in S
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L_14_09 - 318N Krische Lecture 14 Th Ch 22 We begin this...

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