COHROHCOHCXCXCClCBrCXCCOCH3HH3CH3CH2CCCOHCH3HH3CH3CH2CCCHOCH3HH3CH3CH2CXXThe final few recipes from Ch. 12 and a general review of important topicsCh. 12 recipesI. Ways of replacing an -OH group with a halogen1oROH2o3oRO-1.TsClpyridine2. Na+X-R-Cl(SN2)R'lgR-Br(SN2)R-X(SN2)RO1.TsClpyridine2. Na+X-R'OHlgOII. Opening oxiranes1. H3O+2. Na+X-O1.Na+X-2.H3O+HRNOTE: The nucleophile adds to theC which is most substituted, anti to the O of the oxiraneAcid-catalyzed ring openingNOTE: The nuclophile goes to the least hindered C of the ring, acid is added after to protonate the O-. Need a strong nucleophile.Nucleophilic ring openingX can be any nucleophile: halides,OH-, water, etc.III. Making and Breaking ethers1. First deprotonate an OH to make a good nucleophileNa +H-Na+NH2-Na or K
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