Help!

i was syncing my brother iPhone for him and as i was syncing his phone my mac died and now all of his purchases are not on his phone and when i look for them on iTunes the titles of the songs are a light grey color and have the syncing arrows next to them. what do i do?!!!! I need to know how to fix this problem because he will be shipping
Off over seas for a year.

If you can't get your Mac working he can download his purchases direct to his iPhone so long as he has iOS4.3.3 or above
Downloading past purchases from the App Store, iBookstore, and iTunes Store