The song capacity for the 16GB iPhone should be about the same as the 16GB iPod Touch, which is up to 3,500 songs.
Music capacity is based on 4 minutes per song and 128-Kbps AAC encoding - actual capacity varies by content.
Up to 3500 songs is also based on having no video or photos.
You can't get caught up with the up to number of songs advertisement, since the actual capacity varies by content.
Are all your songs encoded 128-Kbps AAC, and do all songs average 4 minutes per song?
It is more important to go by the storage capacity that your songs take up, which you can determine with iTunes - for all music, or by playlist, etc.
You won't have a full 16GB of storage capacity either. This is the decimal equivalent, which is not the actual. The actual storage capacity for my 8GB iPhone is only about 7.3GB. This takes into account the difference between the advertised storage capacity and the actual - which is less than advertised for all hard drives and flash drives. The same applies to your hard drive's actual capacity on your MacBook. And OS X takes up roughly 500MB or so of the actual.