CHEM164 Final: 1-15 C263 Lecture Template Alcohols, Ethers, Epoxides.pdf
12 Jun 2015
School
Department
Course
Professor
Document Summary
Lecture notes chapters 11,12, and 14: alcohols, ethers, and epoxides (review, in part!: alcohols and ethers. Bidensyneoside b glycosidic natural antiallergenic (from bidens parviflora wild) Crown ethers: synthetic ionophores (nobel prize to pedersen, cram, and lehn, 1987) O furan pyran tetrahydrofuran oxirane or ethylene oxide (an epoxide) Alcohols are weakly lewis basic (typical of oxygen lone pair): Alcohols are also weakly br nsted acidic (pka ~ 16-19, similar to h2o): Acidity (pka): hoh (15. 7) > etoh (17) > rc ch (25) > h2 ~ r2nh (35) > r h ( 50) Hydrogen bonding: strongly dipolar o h bond creates extensive bonding interactions: Synthesis of alcohols: review for some (i hope) (1) acid-catalyzed hydration of alkenes. A reaction of limited utility due to competition from the reverse reaction (sn1 elimination) and carbocation rearrangements. Chemistry 263 (2) oxymercuration and hydroboration of alkenes. R: b2h6 or bh3 thf (1/6 or 1/3 equiv, resp. , h2o2, naoh, h2o.
