Dolbier HW Solutions 229

Dolbier HW Solutions 229 - 223 ALKYNES The alkylating agent...

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The alkylating agent, 1-bromobutane, is prepared from 1-butene by free-radical (anti- Markovnikov) addition of hydrogen bromide. Once 1-hexyne is prepared, it can be converted to 1-hexene by hydrogenation over Lindlar palladium or by sodium ammonia reduction. ( f ) Dialkylation of acetylene with 1-bromobutane, prepared in part ( f ), gives the necessary ten- carbon chain. Hydrogenation of 5-decyne yields decane. ( g ) A standard method for converting alkenes to alkynes is to add Br 2 and then carry out a double dehydrohalogenation. ( h ) Alkylation of the triple bond gives the required carbon skeleton. Hydrogenation over the Lindlar catalyst converts the carbon carbon triple bond to a cis dou- ble bond. H 2 Lindlar Pd C CCH 3 1-(1-Propynyl)cyclohexene ( Z )-1-(1-Propenyl)cyclohexene C CH
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