What happens in this reaction and why? 3-methylbutane-1,3-diol + cro3 -->

Here we have to explain and get the product of the reaction between 3-methyl-1,3-diol and chromium-tri-oxide (CrO₃)

The reaction between 3-methyl-1,3-diol with chromium-tri-oxide (CrO₃) form 3-methyl-3-hydroxybutanal.

The CrO₃ is used as a mild oxidant to the alcohol. It only produces aldehyde or ketone depending upon the position of the -OH group in a secondary or primary alcohol.

Here we can see there are two hydroxy (-OH) group in the reactant. However one of the hydroxy is at terminal carbon atom, thus primary alcohol and other in between as tertiary alcohol.

As the reagent CrO₃ does not reacts on the tertiary -OH group thus the -OH group present at 3 position will not be oxidized. Thus only the terminal hydroxy group will oxidize to form the corresponding aldehyde.

Henceforth the final product of the reaction is 3-methyl-3-hydroxybutanal as shown in the figure.  

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