When I try to sync my ipod, itunes tells me certain songs could not be found

I have just tried to sync my ipod on itunes, and a screen comes up to tell me that over 100 songs from my library cannot be synced as they could not be found.......
They all appear in my music library, and in their relevant playlists, only now they all have an exclamation mark just to the left of the title.
Some I have ripped from cd's and some are ones I have purchased thru the itunes store, and it is these I'm most annoyed about, as I paid to have them and now cannot play them.
What can I do to get them to be able to play again?
Neither the ipod or the laptop are new to me, I have been using both successfully for a number of years with no problems.
I have tried de-authorising and then authorising my laptop, and have also restored factory setting on my ipod, but nothing seems to work.......
Any suggestions, please?
Thanks

That exclamation point means the song files cannot be found, for some reason. They are no longer where iTunes expects to find them. They were either moved or deleted. Sometime, a data corruption issue on your hard drive can make files inaccessible. You may want to check that possibility, because other files may be affected.
Since you can still see the name, artist, and album of the missing songs in iTunes, you may want to try using Windows to do a general search of your hard drive volume, searching on the name of one of the songs (or artist or album name). If you are using the default settings for iTunes, iTunes uses the name of song, album, and artist to name the file and directory path of the song file's storage location. If they got moved for some reason, you may find the path to all of the missing songs by finding one song. You can then move them back to the location where iTunes expects to find them.
some are ones I have purchased thru the itunes store, and it is these I'm most annoyed about, as I paid to have them and now cannot play them.
Don't be mad about those songs... Any previous song purchase from the iTunes Store can be re-downloaded at any time at no cost. Go to the main iTunes Store screen. On the right side, find Purchased under QUICK LINKS. On the Purchased screen, click on Music and find those missing songs. There is a Not on This Computer filter there that would be useful in this case. Next to the song name, you should see a button with a cloud symbol. Click it to download that song.

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Thank you for the details of the issue you are experiencing when syncing your music to your iPhone. It sounds like iTunes is not able to locate the original file for the song to transfer it to your device. I recommend reviewing the following articles to locate you music files on your computer:
iTunes: Finding lost media and downloads
http://support.apple.com/kb/ts1408
Where are my iTunes files located?
http://support.apple.com/kb/ht1391
Thank you for using Apple Support Communities.
Best,
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When I try to sync my ipod, itunes tells me certain songs could not be found

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