10-27-08 - 318M Krische, Lecture 27: M - 10/27/08,...

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We considered the reaction of tert -butyl alcohol with HCl to produce tert -butyl chloride. Based on our understanding of mechanism, we were able to predict the 3-step mechanism of this reaction. Each individual step of the mechanism were ones that we had encountered before. Thus, even though this reaction was new, it was operating by familiar principles. We also considered the reaction of HBr with n -butanol to provide 1-bromobutane. Predicated on our understanding of mechanism, we were able to predict the two-step mechanism of this reaction. For both reactions, the poor leaving group (ROH) is converted to a good leaving group (ROH 2 + ). These reactions are essentially S N 1 (for tertiary alcohols) and S N 2 reactions, where the hydroxyl group serves as a latent leaving group that is activated upon protonation. As usual, beware of 1,2-shifts. They will occur when S
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10-27-08 - 318M Krische, Lecture 27: M - 10/27/08,...

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