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Dolbier HW Solutions 425 - 519 CARBOXYLIC ACIDS(c Cyanide...

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( c ) Cyanide ion is a good nucleophile and will displace bromide from bromoacetic acid. ( d ) Cyanoacetic acid, prepared as in part ( c ), serves as a convenient precursor to malonic acid. Hydrolysis of the nitrile substituent converts it to a carboxyl group. ( e ) Iodoacetic acid is not prepared directly from acetic acid but is derived by nucleophilic substi- tution of iodide in bromoacetic acid. ( f ) Two transformations need to be accomplished, bromination and esteri fi cation. The correct sequence is bromination followed by esteri fi cation. Reversing the order of steps is not appropriate. It must be the carboxylic acid that is subjected to halogenation because the Hell Volhard Zelinsky reaction is a reaction of carboxylic acids, not esters. ( g ) The compound shown is an ylide. It can be prepared from ethyl bromoacetate as shown The fi rst step is a nucleophilic substitution of bromide by triphenylphosphine. Treatment of the derived triphenylphosphonium salt with base removes the relatively acidic proton, form-
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