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Dolbier HW Solutions 420 - 514 CARBOXYLIC ACIDS Either of...

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Either of the two following procedures is satisfactory: ( e ) Dehydration of 2-propanol to propene followed by free-radical addition of hydrogen bromide affords 1-bromopropane. Once 1-bromopropane has been prepared it is converted to butanoic acid as in part ( d ). ( f ) The carbon skeleton of butanoic acid may be assembled by an aldol condensation of acetaldehyde. Oxidation of the aldehyde followed by hydrogenation of the double bond yields butanoic acid. ( g ) Ethylmalonic acid belongs to the class of substituted malonic acids that undergo ready ther- mal decarboxylation. Decarboxylation yields butanoic acid. 19.18 ( a ) The Friedel Crafts alkylation of benzene by methyl chloride can be used to prepare 14 C-labeled toluene (C* 14 C). Once prepared, toluene could be oxidized to benzoic acid. Benzene Toluene CH 3 Benzoic acid CO 2 H Methyl chloride CH 3 Cl AlCl 3 K 2 Cr 2 O 7 , H 2 SO 4 H 2 O, heat * * * heat
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