I am trying to form 1,5-pentadiol by using only ethane as a source of carbon. I'm allowed to use any inorganic reagents. I can figure out how to get to a hexane; I heat the ethane to 750C to form ethene, then add water and acid to form ethanol and oxidize this with PCC, while simultaneously adding bromine and then magnesium to another sample of ethane to form a Grignard reagent, then adding the two together.
Sorry, that's a bit confusing. Ideally, I'm going from ethane to oxane (oxacyclohexane) using only ethane and whatever inorganics I need. I can get from 1,5-pentadiol to oxane, but I can't seem to work it back any farther. Any hints would be appreciated.