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Table of Ka Values Acid-Dissociation Constants of Representative Alcohols Alcohol Structure methanol ethanol 2-chloroethanol 2-2-trichloroethanol isopropyl alcohol t-butyl alcohol cyelohexanol phenol Comparison with other acids water acetic acid hydrocholric acid Ka pKa METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date) ELECTROPHILIC AND NUCLEOPHIC CARBON Methylmagnesium bromide Methyl lithium Methyl chloride TYPICAL ELECTROPHILES Methyl chloride acetone Alcohols, carbonyl compounds and carboxylic acids: REDUCTION Reduction: Addition of H2 (or H-), loss of O or O2; loss of X2 Primary alcohol Aldehyde Carboxylic acid must convert OH to leaving group Secondary alcohol Ketone must convert OH to leaving group Teritiary alcohol Lithium aluminium Sodium borohydride hydride aldehyde reduces Comparison of Reducing Agents ketone reduces ester Acid (anion) ease of reduction • LiAlH4 is stronger. • LiAlH4 reduces more stable compounds which are resistant to reduction.