Issue with output from Audacity

Follow the tutorial that tt2 has put a link to, which explains how to split up the track.

Take note of the following, none of which is difficult:

• • open the one-track file in Audacity and immediately create and edit the new copy of it. Use the new copy as the one you will edit and cut up, in case you make any irretrievable mistakes. If you do, at least you can re-copy the original file rather than having to record the vinyl again
  • you will be able to label each track with the appropriate details when you export it from Audacity. (You could use this opportunity to export the new file as an MP3, which is more versatile and takes up less storage space. An MP3 file can store artwork inside the file for example, which a .wav file cannot do. Your choice)
  • each newly created track will need to be imported into iTunes as a new file

I hope it goes well (and why shouldn't it?)

See https://manual.audacityteam.org/man/splitting_a_recording_into_separate_tracks.html.

tt2

If iTunes tells you it cannot locate the file, that means that either the file has been moved, renamed or deleted since you added it to your iTunes Library. So this leads to the question "what are you, or one of your programmes doing to the file after you add it to iTunes?"

I assume that your turntable is creating the file as a .wav file, as well as choosing the location for that file it creates, leaving you with little choice in the matter. If this is what happens, and you then add the song to your iTunes Library (or the turntable's programme does it for you) and you subsequently move, or rename the file, that's why iTunes can no longer play the song.

If that is what is happening, then either move or rename the file before adding it your Library, or follow the iTunes prompts to locate the file in its new location (or by its new name). Once added, don't edit the file. Instead, edit the song, in your iTunes Library.

If iTunes can play the songs, then it should be able to sync them too. What is the exact message you get when it cannot sync these songs?

Ah! Here's a question: are you 100% positive that the message is referring to these new songs? Imagine for example, that your new songs are not set to Sync to your iPod (see below), but the message you see may be referring to other songs. It should be possible to expand message an see a list of songs that did not sync due to an error.

Common reasons why songs don't sync to an iDevice (iPod, iPad, iPhone...):

• if you are using the option to Sync only ticked songs and videos, but these new songs are not ticked, they will not be added to your device. There is no error message for these songs, because your choice is not an error. Check - look in the Songs View, are the songs ticked (checked)? If not, click on the tick-box to turn them on and then try another Sync
• if you using the option to Sync selected playlists, albums, artist and genres, the songs must be in at least one playlist that will be synchronised with your device and they must be in that list before you start a Sync
• if you add the songs to your iTunes library while your device is connected, then those songs probably will not be copied to the device at this sync, because the sync had finished before you added them to iTunes. Solution - add songs to your library and then use Sync afterwards
• the Sync process is broken. Unfortunately, there have been issues with the Sync process for a long time now, whereby random songs do not get added to a device even though they should be. (When looking at the content of the iPod from iTunes, they appear as greyed-out songs, but are usually listed on my iPod, But when asked to play, they get greyed out.) A second Sync can possibly correctly add the rogue songs, but in my experience, iTunes may or may not add them, but will almost certainly remove others, for no know reason. See this post; https://discussions.apple.com/thread/250503104?answerId=250961672022#250961672022 on the subject. Note that the response is from tt2, who has contributed to your discussion. (I have never managed to resolve this issue, I still suffer from erratic syncing.)