Why i am not able to put a pdf format on iBook from itunes?

I tried to put a textbook that is in pdf format in my iPod in iBooks but I am not able to put it there. As much as I try to sync it, it does not work. Why is it like that and what should I do?

I plugged my iPod with the computer, I opened iTunes, I clicked on Books at the top, I put my file there and I selected the books that I wanted to have in my iPod. Then, I clicked Sync. Afterwards, my older books were still there in the iBooks application in my iPod. However, the new book that I put was not there and I don't get why. What I mean by iBooks app is the application that I downloaded from app store and this is where I put my books and my pdf format files. However, I am not able to put this book.

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