IPod touch won't sync all songs in playlist

My son bought a brand-new iPod touch yesterday. He has been trying to compile his playlist and sync it to the new iPod. He has 41 songs on his playlist and only 22 of them will sync. They are all in the iTunes library and the iPod library, but not on the playlist. We tried changing Settings>Music>Group by Album Artist>Off, and that doesn't work. We've also created new playlists and tried syncing those, and that doesn't work either. Today, I noticed that my iPod Touch is doing the very same thing. We have the most recent software and many of the songs were purchased directly through iTunes.
Any thoughts? We've had my son's iPod for 2 days and there is ABSOLUTELY NO WAY I am paying Apple support for help on something that seems to be an inbred error on their part.
Thanks in advance!

I had the same problem as well and tried so many of these solutions, but no luck. I just got a new laptop with windows 8 and when I hooked my iTouch4 to my computer it only show 36 songs out of 509 of the ones I have on my iTouch. (I was freaking out because I thought windows 8 had something to do with it, but as usual I was being paranoid )
I found a way to put the rest of my music on my USB and hooked it to my laptop and put that music in a separate folder. I had all of them play onto iTunes. Now they all worked on iTunes, but I realized they didn't really sync onto my iTouch. To test it out a bought a new song on iTunes and clicked "sync" onto my iTouch, but nothing happened.
So I started searching for answers, but none of the methods solved my problem. So I started messing around with it and realized that the problem was ACTUALLY A SIMPLE SOLUTION.
So this is what I did...
1) Start playing one of the songs that won't sync to your iTouch4
(don't know how to sync all songs at once yet)
2) Now right click at the top bar of iTunes where it shows the song playing
right click on album picture
3) Then scroll to "Add to Playlist"
the arrow of "Add to Playlist" will show a list of your own playlists and the name of your iPod
4) Click on the name of your iPod      Ex) Robert's iPod
5) Then (you can stop playing song at this point) click on iPod device
This should right away take you to "Summary"
6) Instead of being on "Summary" look for "On This iPod" - Click it
7) Now "On This iPod" show a list of all the music that is currently on your iTouch
(including the song you just added from iTunes by following these steps)
8) Make sure all the songs you want in the list have been marked with a "check mark"
9) Then click "sync"
Check iTouch to see if song downloaded...
*If not then - still on "On This iPod" - click on "Autofill"
(Wait for it to load)
Now click "sync"
You should now have the songs on your iTouch as well!
It's a simple solution, but I haven't seen anyone advicing it and I wish they had so I didn't have to go through all this trouble
Hopefully this helps!!!

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