The sodium iodide test would give a precipitate (before or after heating) for

bromobutane

1-bromopentane

2-bromopentane

2-chloro-2-methylbutane

How would I determine whether or not a precipitate will form if I can't do it experimentally?

It's not the same as simply looking at a solubility table, can anyone point me in the right direction?

1-bromopentane and 2-bromopentane results would be the same as they have the same chemical formula right?

so any ideas on how to solve this problem would be appreciated!