Why are song purchased on my imac not automatically downloading on iphone 5?

After an update I noticed my itunes on my iphone 5 was all in disorder. The purchase playlist that has always been automatic/updated on it's own now was all messed up. Album art wasn't correct. I seemed to fix the problem by doing a backup. Now when I purchase a song via itunes on my iMac the song doesn't automatically download/sync with my iphone.
When purchsing a song it would download onto my mac then be on the playlist "Purchased". Without me having to plug in the phont to the Mac.. unsure what happened or how to fix this.

Try a reset ..
Press and hold the Sleep/Wake button and the Home button together for at least ten seconds, until the Apple logo appears.
If that doesn't help, tap Settings > General > Reset > Reset All Settings
No data is lost due to a reset.

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Connect the device to your computer.
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Select iPhone, iPad, or iPod in the Devices list.
Click the Summary tab and select "Manually manage music and videos".
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Why wont songs purchased from itunes transfer to my media files on pc?

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I'm a bit confused by your question.
You say you have synced with your iMac, and that you have match turned on. If match is turned on you can't sync music any more.
Are the purchases new, or old ones?
Can you confirm that match is turned on on both the iMac and the iPhone.

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Try:
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Reset iOS device: Hold down the On/Off button and the Home button at the same time for at
least ten seconds, until the Apple logo appears.
- Unsync all music and resync
- Reset all settings
Go to Settings > General > Reset and tap Reset All Settings.
All your preferences and settings are reset. Information (such as contacts and calendars) and media (such as songs and videos) aren’t affected.
- Restore from backup. See:
iOS: How to back up
- Restore to factory settings/new iOS device.
If still problem, make an appointment at the Genius Bar of an Apple store since it appears you have a hardware problem.
Apple Retail Store - Genius Bar
If necessary
You can redownload most iTunes purchases by:
Downloading past purchases from the App Store, iBookstore, and iTunes Store

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Hello RumDog,
I think this article will help you find the media in your library.
Where are my iTunes files located?
http://support.apple.com/kb/ht1391
Discovering and changing the iTunes Media folder location
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Mac OS X: Click the iTunes menu and choose Preferences.
Windows: Click the Edit menu and choose Preferences.
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From: Where are my iTunes files located?
http://support.apple.com/kb/ht1391
Cheers,
Sterling

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Why are song purchased on my imac not automatically downloading on iphone 5?

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