How can I delete an old file from my library on iTunes

Occasionally I have to replace PDF manuals with ones that have been updated.  But after I sync the new file the old one remains on my Mac itunes library.  How can I delete the old file?  So far all I do is deselect the old file but it's still there.  Sooner or later there will be more old files then current ones making it hard to manage.
Thanks in advance.

You can do this with or without the iPad connected to your Mac.
Launch iTunes on the Mac. Click on Books under the Library heading. Click on the PDFs. Then click on the PDF that you want to delete in order to select it, and go to Edit>Delete and follow the on screen prompts.
if you are using iTunes 11 and do not have the sidebar enabled, and wish to do so, go to View>Show sidebar or use the keyboard shortcut OPTION+Command+S.
If you do not want to enable the sidebar, the library items can be accessed in the button in the upper left corner of the iTunes window.

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