[RaZ]

This should be fairly straightforward hopefully but I'm just wondering if you wanted to add an acetate group to the methyl group (as in the picture posted), how would the reation happen?  Would you first get a tautomer where the double bond would travel to the outside methyl group and then this would attack an Ac2O (acetic anhydride)?  Thanks.

[movies]

That wouldn't work the way you have it drawn.  You would have to use some sort of oxidizing agent because that carbon goes from the alkane oxidation state to the alcohol oxidation state.