iPhone 4 OS 4.1 Pictures

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I am not sure if this is really a newbie question but here is my issue. I had pictures on my iPhone and they were taking up quiet a lot of space, so i decided to delete them. So i went and deleted them one by one by touching the trashcan in the bottom right corner.

after i did all that iTunes still tells me i have over two hundred photos taking up space. No idea where those are. I have 23 of the factory background pictures and the phone tells me there are no pictures in the camera roll. ***?
 
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Your Mac's Specs
13" MBP 2.3Ghz i7 32GB 1TB | iPhone XR
When you plug it into iTunes what happens after you press sync? Does it throw up any error messages? If you open the iPhone as a removable drive on your desktop or in My computer are there any of the camera roll photos in there?
 
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when i sync it no error message comes up. i use a mac and iPhoto opens up. so i do the transfer and as it prompts me whether or not to delete the photos from the iPhone i choose to delete photos upon completion of the transfer.

Transfer completes and selecting the device in iPhoto shows that there are no pictures as well.
 

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