HT201272 My music will not go onto my Ipod.  It is missing in my stuff on Itunes

Help please.  I'm very new to this Ipod stuff and so is my 10 year old.  I have sharing on all my computers but when he plugged his Ipod into one of them it deleted all his music.  I can not put his music back on his Ipod...
Please and thank you.

There are no error messages and yes the iPod is signed into the account that the music was purchased from but what happens is I sync my iPod and it tells me all my music is on there, but it is not in the library and if you search one of the purchased songs it shows up on the iPod. And everytime I click on the song that comes up after searching it takes me to my library for about 5 seconds then puts me at the home screen

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