I suggest you check [http://www.ifixit.com/Guide/Repair/Installing-iPod-5th-Generation-Video-Headphone-Jack-and-Hold-Switch/604/1|iFixit's Guide] for that repair
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I suggest you check [http://www.ifixit.com/Guide/Repair/Installing-iPod-4th-Generation-or-Photo-Headphone-Jack/388/1|iFixit's Guide] for that repair
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Also you could look at [http://www.ifixit.com/Guide/Repair/Installing-iPod-4th-Generation-or-Photo-Headphone-Jack-Bracket/389/1|this one]
I suggest you check [http://www.ifixit.com/Guide/Repair/Installing-iPod-5th-Generation-Video-Headphone-Jack-and-Hold-Switch/604/1|iFixit's Guide]
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I suggest you check [http://www.ifixit.com/Guide/Repair/Installing-iPod-5th-Generation-Video-Headphone-Jack-and-Hold-Switch/604/1|iFixit's Guide] for that repair