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12 - METHODS FOR THE SYNTHESIS OF ALCOHOLS(to date OH I OH...

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R O R Na OH R R R O H O R OH H R OH R METHODS FOR THE SYNTHESIS OF ALCOHOLS (to date) Ketones Aldehydes epoxides I OH - OH 1. BH 3 OH 2. NaOH/H 2 O 2 H + /H 2 O OH OH OH 1. OsO 4 2. H 2 O 2 OH OH 1. mCPBA 2. H + /H 2 O SYN ANTI
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ELECTROPHILIC AND NUCLEOPHIC CARBON Methylmagnesium bromide Methyl lithium Methyl chloride Mg Br H 3 C d - d + Li H 3 C d - d + Cl H 3 C d - d +
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Methyl chloride Cl H 3 C d - d + O d + d - acetone TYPICAL ELECTROPHILES
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Alcohols, carbonyl compounds and carboxylic acids: REDUCTION R C O OH LiAlH 4 R C O H R C O R' NaBH 4 NaBH 4 R C OH H H R C OH H R' R C OH R" R' R C H H H R C H H R' R C H R" R' Primary alcohol Secondary alcohol Tertiary alcohol Aldehyde Ketone Carboxylic acid Reduction: Addition of H 2 (or H - ), loss of O or O 2 ; loss of X 2 must convert OH to leaving group or Raney Ni/ H 2 or Raney Ni/ H 2 must convert OH to leaving group Li Al H H H H Na B H H H H Lithium aluminium
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