Chewing medications instead of swallowing ...?!

No, it is not okay. Pills are designed, even if they aren't controlled release, to be digested at a certain rate. That's why you can go for six or eight hours between aspirin pills: they take that long to digest, be absorbed, and then excreted.

If you chew pills, it increases the total surface area that stomach acid can act on, meaning that instead of taking three hours to digest a pill, it might happen in half an hour. There is no guarantee that your body can absorb the medication at that increased rate, so most likely some is being lost.

It would make the pill work faster, but it would not last as long, and probably would not be as effective.

It can cause damage to the stomach and/or esophagus.

The medications are usually supposed to be taken with water, to dilute them and for absorbing them.

The concentrated medication in the wrong place can actually burn the linings of the esophagus or stomach.

No wonder he has digestive problems.