Given that all the injuries are on the left side, I'll venture that he went down to that side. It could be that he tried to catch himself with his left arm ( dangerous no-no if there's any speed involved) and drove the arm up injuring the shoulder. Or he might have tried to keep the arm in and take the impact on the hip and shoulder, and gone down hard. The second scenario usually breaks collar bones, not shoulders, but a bit of twist or body angle can make a world of difference.

It's also possible that he had an endo with a 1/2 twist. This happens if you overuse or lock the front brake while trying to turn. It throws you over the bars but at an angle to the outside of the turn (aka high side dump), body slamming you to the pavement on a shoulder or the side of your head. Unlike a low side dump, there'll be very little road rash, but it's more likely to break stuff.

There's also the likelihood that his bones are weaker or more brittle than those of a younger man, which doesn't help.

Either way, I feel for him. I've had my share of crashes, but so far have been lucky and not broken anything, I just leave blood trails as I limp away.