My mom is a school counselor and sees lots of this.
Some of what other said are what she has said they struggle with... mostly the structure of the day and classroom, asking permission for little things like sharpening a pencil or going to the bathroom, and having to be ready for a quiz/test/project on a certain day without being able to just reschedule because they didn't do the work.
Lots of kids successfully make this transition though... and even if you didn't do it now, some of these things would come up for college anyway. So it's not bad.
Definitely tour the school when class is in session, and maybe sit in on a lesson to see how the classroom is structured. That way he can come up with his own questions, and maybe meet a couple kids.
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