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Use sodium amide to deprotonate acetylene and react it with iodoethane (or equivilent) two times to form 3-hexyne. Use sodium amide again to "move" the triple bond to a terminal position (to make 1-hexyne). Reprotonate with dilute HCl. Now simply do a hydrobroation-oxydation (BH3*THF followed by H2O2 and NaOH(aq)) to yield hexanal.

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Q: Synthesis of hexanal by use acetylene and alkyl halide?
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