In my basic organic chemistry class, I learned that only primary and secondary alcohols undergo oxidation (using $\ce{KMnO4}$).

However, what is the outcome of reacting tertiary alcohol (1-methylcyclopentanol) with a strong oxidant like $\ce{KMnO4}$ with no heat?

P.S. I am specifically interested to know what happens with no heat, because according to my minimal knowledge I know if heat was added then it is dehydration.


1 Answer 1


There is no reaction. t-BuOH may be used as a solvent for permanganate reactions. For example, see Abiko et al. [1].


  1. Abiko, A.; Roberts, J. C.; Takemasa, T.; Masamune, S. $\ce{KMnO4}$ Revisited: Oxidation of Aldehydes to Carboxylic Acids in the Tert-Butyl Alcohol - Aqueous $\ce{NaH2PO4}$ System. Tetrahedron Letters 1986, 27 (38), 4537–4540. https://doi.org/10/c3t9xj.
  • 1
    $\begingroup$ When do organic compounds get oxidized to CO2 then? $\endgroup$ Jun 28, 2019 at 19:25
  • 2
    $\begingroup$ When you use forcing conditions: high temp. conc reagents. The OP asked about reactions without heating. $\endgroup$
    – Waylander
    Jun 28, 2019 at 20:59

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