Why do books not sync with an iphone sync to macbook pro?

Sometimes, but not all the time, when I sync my iPhone 5s to my MacBook Pro 2007 using iTunes, all my previously selected books and PDFs are all unselected. Then I have to go and reselect each book and PDF I want to sync again, and there are a lot of them.
Another question is how do you delete books or PDFs from the computer permanently once it is there?
thanks,
Mark

Sorry I meant Contacts not Diary

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Dylrob wrote:
Apfelwurm wrote:
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Dylrob wrote:
Apfelwurm wrote:
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Why do books not sync with an iphone sync to macbook pro?

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