[mkrcc12]

I have a study guide here for my final and there is one question that is boggling my mind. How would you draw a butylcyclobutyl ketone? I know to draw the four carbon ring but where do I put the ketone functional group and the extra butyl group?

[Dan]

There are a number of geometric isomers. "Butylcylobutyl ketone" is not specific enough for you to tell.

For example, 3-n-butylcyclobutyl ketone would be an example of a specific structure. How would you draw that?

[movies]

An informal naming of 2-butanone is "ethyl methyl ketone," it's certainly not IUPAC nomenclature, but you do see that sometimes.  In that case you should be able to figure out where to put the other groups.  Of course there are still the structural isomer problems Dan mentioned.

[Custos]

That interesting - there are two ways to interpret the nomenclature question. If it's a IUPAC name with some detail left out, as Dan suggested the compound could be the one on the left (or the 2 isomer)... ignoring the other possible butyl isomers. But if it's referring to the old-style convention for naming ketones (eg. benzyl methyl ketone instead of phenylpropanone) it could be the structure on the right. Don't you just love the ambiguity of different naming systems?

[mkrcc12]

I'm thinking it's the old way and the one on the right is going to apply. Thanks a lot for the help.