Transfer files to external HD -- transfer starts but doesn't complete

I have a 2011 Macbook Pro and an older (5 year old) Western Digital external hard drive. I have always used this hard drive for both mac and windows. Recently, however, whenever I go to transfer a file from the mac to the WD hard drive, the little transfer window pops up and it appears to initiate the transfer. However, it never fully starts it. It appears to "get stuck" in that initiating stage, showing zero of 3.16 gb transferred and shows an unknown transfer time. This happens no matter how long I leave it open. Again, I have used this external hard drive with my macs for the past 5 years without any problems until now. I haven't moved or modified the WD hard drive, so I am not sure what happened or how to solve this problem. Any suggestions??
I appreciate any help you can give me!!
Have a great day!

I've not encountered this, but I an suggest a few possible fixes.
1. Download an appropriate driver from WD. That might fix the problem.
2. Investigate if the problem occurs with Mac and Windoz. If it affects both, the HD may be the issue.
3. Download Kext Wizard and install. It's a utility not unlike Disk First Aid, but faster, and more applicable to your issue. http://www.insanelymac.com/forum/index.php?showtopic=253395
Post your results; sounds interesting.

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When I plug in my iPhone to sync, it starts but does not complete the process and several pieces of data are not being transferred to my iPhone from my MacBook Air.

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When I plug in my iPhone to sync, it starts but does not complete the process and several pieces of data are not being transferred to my iPhone from my MacBook Air.
Any help that you can provide in helping my iPhone accurately sync with iPhoto and iTunes will be greatly appreciated.
Symptoms:
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apple icon
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Other Potential Pertinent Info:
The flash memory hard drive on my MacBook Air recently died (perhaps a month or two ago). Apple had emailed me about a known issue and literally the next day, my MacBook Air crashed. I installed a new flash memory drive and re-installed everything from a backup off of an external hard drive. Everything seems to be working fine; it recreated accurately all of my software and data, including iPhoto and iTunes, the pictures and songs (respectively) for which are stored on that hard drive, as opposed to being on the flash memory in the MacBook Air itself. However, I don’t recall if the start of the sync problem described herein started happening at the same time that I replaced the flash memory drive. All I know is that the computer is working perfectly in all respects and that even as the sync is failing, it at least says that it’s doing the right things and looking in the right places (e.g., the list of albums on my iPhone matches the list of albums in iTunes, etc.).
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OSX v. 10.9
iPhoto ’11 v. 9.5 (902.7)
iPhone iOS 7.0.4
iTunes v. 11.1.3 (8)
Summary Tab
Backups (This Computer)
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Automatically sync when this iPhone is connected
Sync only checked songs and videos
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Selected albums, Events, and Faces, and automatically include (no Events)
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ITune download continues to process but doesn't complete. What could be the issue

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