Aldol of 7-oxooctanal
If in doubt, draw:



Deprotonation at C-6 under thermodynamic control results in the more stable enolate (1c) and leaves the aldehyde (= the centre with the higher carbonyl activity) intact for the aldol reaction. 

As already outlined by Uncle Al, the product is likely to undergo elimination to furnish acetylcyclohexene.

However, if that is your target molecule, addition of acetylene to cyclohexanone, followed by an acid-catalyzed rearrangement of the propargylic alcohol would be an alternative route.