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We were required to find the number of moles of $CrO_3$ required to oxidize 6 moles of heptan-2-ol. I tried balancing the equation but I am not aware of the final chromium containing product. Knowing the mechanism would help answer this questions quickly but I was unable to find it in any source I have access to. Can someone help? Thank you.

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  • $\begingroup$ Are there given the reaction conditions? $\endgroup$
    – Poutnik
    Commented May 17 at 6:13
  • $\begingroup$ No they weren't mentioned in the question :( $\endgroup$ Commented May 17 at 7:48
  • $\begingroup$ Though in our curriculum, we take the solvent medium as acetone unless mentioned to be acidic. $\endgroup$ Commented May 17 at 7:49
  • $\begingroup$ Does this help? $\endgroup$
    – user55119
    Commented May 17 at 14:13
  • $\begingroup$ Yes, thank you so much! $\endgroup$ Commented May 17 at 14:17

1 Answer 1

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The Name Reactions webpage gives acceptable mechanism to Jones Reaction, which is an organic reaction used to oxidize organic alcohols using chromic trioxide $(\ce{CrO3})$. in the presence of acid (often $\ce{H2SO4}$) in water. The mechanism begins with the reaction of $\ce{CrO3}$ with acid $(\ce{H2SO4})$ to form chromic acid or dichromic acid in more concentrated solutions:

Mechanism of Jones Oxidation-Cromic acid

The $1^\circ$- or $2^\circ$- alcohol oxidation then occurs with newly formed chromic acid which in turn gets reduced in the process (Ref.1). The oxidation of $2^\circ$- alcohol is shown in following scheme:

Mechanism of Jones Oxidation-Alcohol oxidation

Since your alcohol is a $2^\circ$- alcohol, you need a little more than $\pu{6 mol}$ of Jones reagent for complete oxidation.


References:

  1. Kenneth Bowden, I. M. Heilbron, E. R. H. Jones, and B. C. L. Weedon, "13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols," J. Chem. Soc. 1946, 39-45 (DOI: https://doi.org/10.1039/JR9460000039).
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