Cyclohexanone undergoes an aldol condensation with hydroxide or alkoxides.
It probably depends on how sophisticated the instructor is. Side reaction is certainly a concern for maximum yield. Could you make the case for adding 1eq of NaH in a sea of CH3
I? Perhaps. Alpha-methylating the ketone might creep in.
Otherwise- he needs to think about protecting group strategy. Mask the carbonyl before alkylating. Certainly makes the assignment more interesting- and shows more sophistication.
By the way--- this is a known compound with actual preps in the literature.