IPhone won't let me sync music to iTunes on my Mac?

Alright I have two iPhone 5s I just use one as more of an I touch and a backup for something that goes wrong. Well a bunch of songs I got on my iPhone (had all of them on both iPhones) but they weren't on my computer so I used my back up one and pressed on transfer purchases and all that happened was it deleting those batch of songs from my phone and there's no way to get it back, I've tried downloading them from "purchases not on this iPhone" but it said everything was downloaded. My other phone still has everything. I got new songs but there on the computer. If I sync it ill get the new songs and lose those batch of songs that deleted off my first phone. And if they get deleted then those songs will be gone forever. What do I do!

You need to get music off your device before syncing with iTunes. On Windows you can do this by using sharepod 3.9.9 However I don't know any similar free program for Mac

  • Why won't my iphone sync to itunes on mac? I'm trying to add songs onto my new iphone 4S but the computer only charges the phone. It won't show up in itunes on my macbook pro. I couldn't find the answer from googling it so posting this question is my only hope to finding the answer. Please
  • Why won't itunes let me sync with my iphone? When I plug in itunes and my phone, i get this error message: "Itune was unable to load data class information from Sync Services. Reconnect or try again." I try many times. After this error message pops up, itunes freezes and i have to go to windows task manager to close it. How do i fix it so i can sync again?
  • Why won't itunes let me sync my iphone? I just added my iphone to this computer and authorized it and everything. It is authorized on 4/5 computers. I have added one song to my list and when i go on 'file' then 'devices' then 'sync' and other options i'm unable to click on it, and its a lighter colour? Why is it like that and how do i change it so i can sync my iphone and its music?
  • My itunes won't let me sync my iphone 5? At first, it said over capacity for the "other" data space. So, like a dumbass, I restored my phone. Now, I have no photos, videos, or songs on my phone. Just my contacts, thanks god! When i connect my phone it recognizes it, but it does'nt allow me to sync it. I finally got it to lower the gb for the "other" data space, but still i can't sync! I'm freaking out here. Lol I need my music.