IPhone 4S not syncing properly?

My Dad has recently traded in his iPhone 4 for the new 4S. He is an avid music lover but hopeless on computers, so he has asked me to transfer all of his 646 songs and 76 apps onto my PC and then sync them onto his new phone. The songs and apps have transferred to the PC perfectly and the iPhone 4S has been set up correctly, but none of the songs will sync onto the new iPhone. All the software is up to date (unless a new version of iTunes was released today) and all the songs and apps seem to be selected for syncing but they just don't seem to be transferring.iTunes just seems to be syncing with the iPhone but not transferring songs.

And yes, all the songs have been purchased off iTunes.

IPhone app trouble not downloading right?

Help I downloaded an app recently and just about when it gets to the end it says the app was unable to be downloaded. If I try to open it it automatically closes. I'm downloading it over 3G but its under 20 mb so it should work fine I've tried turning it off and on and resetting the app but nothing works what is wrong

My iphone 4 won't work with my stero?

I have a sony stero w/ ipod/iphone doc i hit the ipod button but i don't get any sound at all, if i put it radio on i get sound so its not the stero. How can i fix this

Iphone won't work through plug-in cassette on radio?

I just recently got an iphone. Its not a newer model. I think its a iphone 2?
Anyways, I have a plug-in cassette that has the wire with the jack thingeh you put into the headphone outlet… It's worked with all my other phones and mp3 players. It won't work with my iphone. The music does not come out of my jeeps speakers and only comes out of the phones speakers. Anyone know why this is? If so could you tell me how to get it to work? If not… What do I need to buy so I can play music through my jeep with my phone.