Exporting playlists with PDFs

I have 2 mac laptops and have recently imported my Itunes library from one to the other (exporting the library, moving it to the other laptop, and then importing it).
However, a few of my playlists mix mp3 and PDFs. On those, only the mp3s were exported correctly. I tried exporting only the playlist as opposed to the whole library, but to no avail.
I can copy the PDFs into the new playlist, but they won't mix with the mp3 in the same order.
As they are language files which go with mp3 lessons, and there are about 1200 of them, putting everything back together in the right order by hand is rather troublesome.
Do you know of anyway to export the whole playlist, mp3 and PDFs, in the right order ?
thanks a lot !

Whoops, I should've been more specific I am not trying to open a file on InDesign. I created an Interactive PDF on InDesign and am now trying to export it so that I can share it with my teacher. The intent is set for web. When I try to export as an Interactive PDF, it will not let me. I get this message when I try- "cannot open the file. Adobe InDesign may not support the file format, a plug-in that supports the file format may be missing, or the file may be open in another application." This could be because I have it set to "Preview after saving". It saves the document but when I try to open the document on my computer to preview it, it won't work.

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