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Toluene can be oxidized to form benzoic acid. do aliphatic alkanes give similar kind of reaction?

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    $\begingroup$ Roughly speaking, aliphatic alkanes don't have any reactions other than combustion. $\endgroup$ Sep 4, 2018 at 9:55
  • $\begingroup$ Not in any useful manner $\endgroup$
    – Waylander
    Sep 4, 2018 at 10:12

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It's tricky, because the bond enthalpies of sp3 C-H bonds are high (so they are hard to break) and because alkanes typically have a large number of CH bonds so selectively oxidizing any one of them can be challenging. Generally speaking the more electron-rich CH bonds (i.e. tertiary positions) are oxidized more easily that less-substituted, less electron rich ones.

TFDO will do it, see here: https://en.wikipedia.org/wiki/Oxidation_with_dioxiranes and there are a bunch of other methods (just try googling "aliphatic CH oxidation").

It's quite a hot area of research, since if you can control it then in theory you can turn feedstocks from crude oil into more useful functionalized molecules.

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