Certain songs wont sync to my itouch

Itouch 5
Windows 7
A couple months ago, I updated my Itouch 5 to IOS 7. I noticed that all the songs that were unchecked were on my itouch. Thinking that maybe I had accidently checked them all again, I didnt see it as a big deal. Two weeks ago, I imported a few songs from some CD's onto my itunes. After seeing it was done syncing, I disconnected it and noticed that none of the songs I imported were there. So I tried syncing again but it didnt work (I have itunes automatically update and sync any songs to my ipod when connected). When it didnt sync I decided to just leave it alone for a couple days and wait until the next time I downloaded a song. A week later, I purchased a song on itunes. I checked to see if it was on recently added like it normally does but it wasnt there. I checked 'Songs' and surprisingly enough it was there. Then today, I went to try to sync my ipod again but nothing happened. Nothing imported to my itouch. And all the songs that I thought I must've checked.....were still unchecked just like I left them. I have tried closing itunes and then opening it again. I've also tried restarting my itouch. Could it possibly be that maybe my wire is worn out and just not working anymore? Or did updating the IOS change something?

Do the songs play in iTunes?
Verify you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod
Try syncing using the manual method

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Thank you for providing the details of the issue you are experiencing with transferring the apps purchased from the iTunes Store. I recommend following the steps in this article:
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http://support.apple.com/kb/ts1389
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http://support.apple.com/kb/PH12113
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Message was edited by: Hilltophoods

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Open iTunes and create a playlist to update your iPod from, call it -My iPod for example (the dash will position it at the top of the playlists in Sources). You can make it a smart playlist that picks the songs for you or just a normal one and drag whatever content you want to have into the playlist. If you are making a smart playlist limit it to just less than the size of your iPod (for example 3700MB for a 4G iPod Nano. Now connect your iPod and when it appears in the Source list click on the iPod icon to bring up the preference tabs in the main pane. Go to the Music tab and choose Sync Music and the Selected playlists radio button. Choose the playlist you just made from the selection and click Apply. You can also sync from any existing playlists by choosing the same setting, you just need to make sure that the size of the playlists don't exceed the capacity of your iPod:
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When you want to change the selection in the smart playlist just delete everything in it and it will add a new selection. When you want to change the normal playlist just delete out what you don't want and drag in a new selection.

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Certain songs wont sync to my itouch

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