CHEM 2020- Final Exam Guide - Comprehensive Notes for the exam ( 246 pages long!)

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Acid catalyzed ring opening of epoxides: epoxides more reactiive than dialky ethers b/c of large strain, epoixdes react in both basic & acidic conditions. In water: acid catalyzed hydrolysis of epoxides gives gylcerols with anti sterochemistry. Inolves protonation of oxygen followed by sn2 attack by water. It produces an alkocy alchohol with anti steiochemistry: used to make compounds with ether with alcohol functional group. Base-cataylzed ring opening of epoxides: ethers do(cid:374)"t u(cid:374)dergo (cid:374)u(cid:272)leophil(cid:272) su(cid:271)sttu or eli(cid:373)iatio(cid:374) u(cid:374)(cid:272)der (cid:271)asi(cid:272) conditions b. c alkodix is poor leaving group, strain in epoxides allows for subs or elim, epoxides are hugher in energy than ether. Epoxides displacement has lower energy: alkocide ions react with epoxides to form ring-opend products, amines can open epoxides. Rxn of epoxide with grignard & organolithum reagents: grignard & organolithim reagents attack epoxides to give ring- opened alcohols. Cleavage of ethers by hbr & hi: alcohols are reactive. Iodine and bromide ions are good nucleuphiles but weak base.

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