[orgopete]

I find two things troubling. Is 4-hydroxycyclohexanone in the Aldrich catalog? Cyclohexanone undergoes an aldol condensation with hydroxide or alkoxides.

[azncuzin202]

Yeah,  4-hydroxycyclohexanone is in the catalogue. http://www.sigmaaldrich.com/catalog/product/aldrich/t292184?lang=en&region=US

[TwistedConf]

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 CH₃I? 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.

[azncuzin202]

Would alpha methylation be guaranteed or would it only give a minor product?