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CHEM 2301 Lecture 22.pdf

CHEM 2301 Lecture 22.pdf - Hydration of Alkenes 1 Acid...

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9 Hydration of Alkenes 1: Acid Catalysed Hydration The general reaction and mechanism will look somewhat familiar. Markovnikov regioselectivity is observed. H OH 2
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10 Hydration of Alkenes 2: Hydroboration We can generate alcohols from alkenes in a two step reaction of general form: Note the regioselectivity: In this case, the –H is installed at the more substituted end, and –OH at less substituted end (this is often referred to as anti-Markovnikov regioselectivity). Borane (BH 3 ) is a powerful electrophile, which is not available in an isolated form, but often as Lewis acid/base complexes: Diglyme = ethylene glycol dimethyl ether, (CH 3 OCH 2 CH 2 OCH 3 )
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