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Chemistry 17 Online
OpenStudy (aaronq):

Organic chem (see picture)

OpenStudy (aaronq):

whats a plausible way to get here? Is E2 then hydroboration able to get the alcohol group there? |dw:1374682036455:dw|

OpenStudy (aaronq):

alcohol then oxidized with KMnO4 or something

OpenStudy (anonymous):

is it a cyclohexane ring or an aromatic core?

OpenStudy (aaronq):

cyclohexane

OpenStudy (anonymous):

let's see now, perhaps saturate it with H2 first, to remove the double bond Then halogenate, tertiary atom would receive the halogen the easiest(the one where the sidechain connects) Treat with KOH to form double bond between the sidechain and the ring. Hydrate, anti-Markovnikov, so that H goes to the tertiary atom, OH goes to the first atom of the sidechain. Then oxidize with KMnO4 to get the ketone.

OpenStudy (aaronq):

that seems reasonable, thanks man. i'm wondering, though, would the halogenation create multiple products?

OpenStudy (anonymous):

It would, but in neglectable quantities, the tertiary halide is the bulk product.

OpenStudy (aaronq):

aight, thanks.

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