Today my professor gave us these examples for Baldwin's rules. However, I can't explain how he named these.

In the first reaction the oxygen anion is acting as the nucleophile, the electrophile is the carbon of the C-Br, which is sp3 hybridized (making it tet). the bond broken during the cyclization is the C-Br which is outside of the ring (exo). I would have named this 5-exo-tet. but he had labeled it as 5-endo-trig. How can this be true? what am i missing

In the second scheme it was dictated as 6-endo-tet. Tet makes sense from the aformentioned logic, however endo does not because the C-Br bond is broken during cyclization. I suppose it is equally logical to say that the C=C pi bond is also broken, but how do you know what to prioritize?

Any ideas would be awesome! Thanks!