Why is your iTunes saying determining tracks to sync?

Your gonna have to do it manually.

Connect your iPod/Device

Under DEVICES

"Click" on iPod/Device or the name you gave your iPod/Device.

In Center of iPod/Device menu screen

Highlight SUMMARY (Not highlighted)

"Click" on SUMMARY

Scroll down to OPTIONS

"Uncheck" the box (Sync Only Checked Music and Videos)

Scroll down

"Check" the box (Manually Manage Music and Videos)

Scroll to lower left corner "Click" Ok

"Click" on MUSIC/MOVIES in iTunes library top lefthand sidebar.

Highlight the File you want

"Click"[Hold] & Drag File to your iPod/Device or the name you gave your iPod/Device.

It should then start to sync to iPod/Device