iTunes not syncing all songs to iPhone

I have 246 songs in iTunes all purchased through the iTunes store. I would sync the songs to my phone and play them all the time, everything worked great. One day I had some issues with my phone and had to restore it, losing all of the songs on it. When I plugged my phone into my computer to sync all the songs onto it again, everything seemed to work properly. It said it synced the right number of songs and gave no error messages. However for some reason several of my songs are not listed on my phone. When I look at the amount of space the music takes up on my computer (1.76GB) my phone has the same amount listed. The songs just are not showing up in my music list. I have gone through every song individually and they are not listed under another artist or title or any other unusual thing. There are several songs affected, around 30 I suppose. I have cleared all the songs off my phone and put them back on again with no change. I have also redownloaded the songs from iTunes but it still will not sync them onto the phone. I have no idea what else I should do next.

Update: I tried to download the missing songs from iTunes on my phone and it downloaded them successfully. This is a possible work around however I do not want to have to do this every time I sync up my phone.