(j)Hydrogenation of the triple bond over the Lindlar catalyst converts the compound to a cisalkene.9.31Ketones such as 2-heptanone may be readily prepared by hydration of terminal alkynes. Thus, if wehad 1-heptyne, it could be converted to 2-heptanone.Acetylene, as we have seen in earlier problems, can be converted to 1-heptyne by alkylation.9.32Apply the technique of reasoning backward to gain a clue to how to attack this synthesis problem.A reasonable fnal step is the formation of the Zdouble bond by hydrogenation of an alkyne overLindlar palladium.The necessary alkyne 9-tricosyne can be prepared by a double alkylation of acetylene.It does not matter which alkyl group is introduced frst.The alkyl halides are prepared from the corresponding alcohols.CH3(CH2)12OH1-TridecanolCH3(CH2)12
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