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How to convert ethanol to 1,1-dichloroethane?

My approach: Convert ethanol to ethene followed by $\ce{HCl}$ addition. But that's no use. Well if it is possible to create gem-diol from here, then maybe it can be done. But not getting a suitable reaction. Can't seem to figure out anything. Please help!

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  • $\begingroup$ Well you have to at least tell us what your thoughts on this is. $\endgroup$ – M.A.R. Sep 2 '15 at 14:12
  • $\begingroup$ Addition of chlorine gas with UV light to methane forms polychlorinated methane, so something alone these lines is nearing your goal. $\endgroup$ – khaverim Sep 2 '15 at 14:26
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convert ethanol to 1,1-dichloroethane?

A standard route for producing gem-dichloro compounds involves treatment of a ketone or aldehyde with $\ce{PCl5}$ (see the second to last paragraph in the "Chlorination of organic compounds" section here and page 18 here).

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(image source)

Therefore, you could carefully oxidize your ethanol to acetaldehyde and treat it with $\ce{PCl5}$.

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