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L_17_09 - chlorotoluene with hydroxide at high temperature...

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318N – Krische, Lecture 17: Tu - 03/24/09, Benzynes, Reduction of Nitroarenes and Amines Today, we began by reviewing the Midterm II examination. Having completed EAS and NAS, we considered “False NAS”. In “False NAS”, haloaromatics are exposed to base under extremely forcing conditions to form the elimination product BENZYNE. The extra pi-bond of benzyne is extremely reactive due to poor orbital overlap. Once it is generated, benzyne will react quickly with other species present in the medium. For example, heating chlorobenzene with aqueous hydroxide at high pressure provides benzyne which, the presence of water, yields phenol. To confirm that these reactions precede by way of the benzyne intermediate, we examined the reaction of ortho-
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Unformatted text preview: chlorotoluene with hydroxide at high temperature and pressure. Two products were obtained: 1-hydroxy-2-methylbenzene and 1-hydroxy-3-methylbenzene. • We wrapped up aromatic chemistry by considering some useful reactions of aromatic compounds. Specifically, we discussed the reduction of nitro-groups using Fe/HCl. Here, we convert the nitro group (a meta-director) to an amino group (an ortho/para director). • We begin Chapter 23 on Amines. Amines are remarkable compounds and have profound biological activities. In class, we took a look at the structures of some of the more “news-worthy” amines such as Novocain, Sudafed, Quinine, etc. ....
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