mass spectral interpretation of cyclohexene including fragments?

Question

I don't know how/where to break open the ring, or which fragments to remove

Answer 1

First thing to look for is substituents on the ring falling off, like if you also have a hydroxy group then you'd look for a mass peak that is smaller by 17 (16+1) from the parent ion. For a cyclohexene ring to fragment in the mass spec you'd have to break the same ring twice, and that's a little hard. If it would break the first place it would probably break is at the double bond.