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 Lindlarpalladium 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 Br2and then carry out a doubledehydrohalogenation.(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.H2Lindlar PdCCCH31-(1-Propynyl)cyclohexene(Z)-1-(1-Propenyl)cyclohexeneCCH
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