What will methyl (2-oxocyclohexyl)acetate produce when reacted with sodium borohydride? What will methyl (2-oxocyclohexyl)acetate produce when reacted with sodium borohydride?



I feel the answer should be 2-(2-hydroxypropyl)cyclohexan-1-one:



Because the carbonyl carbon on the aliphatic chain should be more electrophilic than the one on the ring due to the presence of two neighbouring electronegative oxygen atoms. Correct me if I am wrong but I think the reaction begins with the hydride ion which acts as a nucleophile? 

On the other hand the answer given in my book is 1-(2-hydroxycyclohexyl)propan-2-one: 



Can someone please help me out here?
Both carbonyl carbons (and everything else in the molecule) are in aliphatic environments.  The six-membered ring you drew is not aromatic, it is saturated like a cycloalkane.

The carbonyl group in this ring is a ketone function, bonded only to other carbon atoms.  The carbonyl group in the chain is bonded to oxygen (did you miss that?) in an ester function, which is a less active electrophile than the ketone function.  Yes the additional oxygen atom is electronegative, but with its octet satisfied it can (to a degree) share a nonbonding pair with the carbonyl carbon, and that effect dominates making the ester carbon less electron deficient. The sodium borohydride reacts accordingly.