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Download Reaction List - Ch 15 Reactions of Alcohols Alkoxides reacting as a
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Transcript
Reaction List - Ch 15 Reactions of Alcohols Alkoxides reacting as a Nu to form ethers base acid Cl OH O or Nu O OTs E alcohol can be methyl, 1o, 2o, 3o, or aryl base can be NaH, Na, K, or NaOH as appropriate alkyl halide or tosylate must be 1o to avoid E2 products Alcohols reacting as bases or nucleophiles to form alkyl halides base OH HX alkyl halide X HI, HBr, or HCl may be used; HCl should be accompanied by ZnCl2 alcohols must be 2o or 3o in order to form C+ rearrangements may occur Nu OH Nu OH PBr3 Br alkyl bromide Cl alkyl chloride SOCl2 pyridine PCl3, PCl5, or P/I2 may be used alcohol must be 1o or 2o since mechanism contains and SN2 step Alcohols reacting as bases to form alkenes base OH H2SO4 alkene alcohol must be 2o or 3o in order to form C+ rearrangements may occur constitutional and stereoisomers may form ether Tosylates acting as electrophiles to make substitution products Nu OH Nu TsCl OTs SN2 E tosylate must be 1o in order to avoid E2 products pyridine Oxidation of alcohols to aldehydes, carboxylic acids, or ketones Collins 1o O OH or PCC 1o OH Jones, etc H O OH 2o Collins, Jones, etc OH aldehyde O carboxylic acid ketone Collins = CrO3, pyridine PCC = CrO3, pyridine, HCl Jones = CrO3, H2O, H2SO4 etc = Na2CrO4 or Na2Cr2O7, and H2O, H2SO4 3o and aryl alcohols cannot be oxidized using these methods Nu ether alkyne nitrile etc
