Question

Using Chemdraw or paper and pencil. Draw the mechanism for the reaction of cyclohexene with potassium permanganate. Upload a JPEG or PDF file as your submission.

Answer 1

The reaction between cyclohexene and potassium permanganate is an example of an oxidative cleavage reaction. It involves the oxidation of the alkene double bond and the cleavage of the carbon-carbon bond, resulting in the formation of two carbonyl compounds.

Here is a step-by-step description of the mechanism:

The potassium permanganate (KMnO₄) dissociates in water to form MnO₄⁻ and K⁺ ions.

The pi bond in cyclohexene acts as a nucleophile and attacks the MnO₄⁻ ion, resulting in the formation of a cyclic intermediate. This intermediate is an addition product of the alkene with a MnO₄⁻ ion.

The cyclic intermediate is unstable and rearranges to form a dihydroxylated product. In this step, one oxygen from the MnO₄⁻ ion adds to one carbon of the alkene, and the other oxygen adds to the adjacent carbon.