[Ak]

CrO3 in acidic conditions with acetone as a solvent at 0°C is used on aldehydes to make carboxylic acids.  My textbook says that the only drawback to this oxidation is that it takes place under acidic conditions and other sensitive molecules will undergo side reactions.  And it goes on to say that carbon-carbon double bonds are sensitive to the acidic conditions.  The textbook does not comment on what these side reactions are.  My question is what happens to a carbon-carbon double bond under these conditions?  Thanks

[azmanam]

hydration, isomerization, and migration into conjugation are 3 that come to mind right away.