CHM136H1 Lecture 33: Properties and Reactions of Alcohols (Apr. 4/16)
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CHM136H1 Full Course Notes
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Document Summary
Str of acid in water can be expressed by acidity constant, ka. Smaller ka and larger pka = less acidic. Larger ka and small pka = more acidic. Electron-withdrawing groups make alcohol stronger by stabilizing conjugate base. They react with alkali metals and strong bases. Below: the more acidic one is on the left. 13 orders of magnitude, for the left the fluorines take e- away from o. Note that both molecules undergo great steric hindrance. Alkoxides are bases used as reagents - displaces h with a metal electrophile, creating a salt. With e-withdrawing sub, they are more acidic than phenol. With e-donating sub, they are less acidic than phenol. Alcohol hydroxyl can be converted to many other functional groups, overview below. In hydroboration of alkenes, indirect methods used to make alcohol are: Direct hydroxylation with oso4 with reduction step of nahso3. Trans-1,2-diols can be prepared from acid-catalyzed hydrolysis of epoxides. Many strategies to identify reactions incl ir spectroscopy.
