Hi ChuC - in short, you are correct, deprotonation of the ketone would result in the formation of an enone. A good example of this is in intramolecular aldol rxns, such as 2,5-hexanedione in the presence of NaOH and ethanol. Deprotonation occurs on the tertiary methyl group of the ketone (in answer to your second question) and results in an intramolecular attack to form 3-methyl-2-cyclopentenone. In rare cases, deprotonation could technically occur at either adjacent carbon (to the carbonyl) forming two cyclic products (i.e., 2,6-heptanedione in the presence of NaOH and ethanol could technically form both 3-methyl-2-cyclopentenone or [2-methylcyclopropenyl]-ethanone => VERY MINOR) but this would be quite rare.

Much of this however would be well beyond the scope of the MCAT, but are rather interesting conceptually. Good question....

-Matt