“Could the chain have been damaged by attempting to use the middle chainring suring one 2 hour ride”
Its more likely to either be:
-You’ve not set the chain to be the correct length for the casette/chainrings [round the biggest chainring, round the biggest rear sprocket (NOT through the mech) and then overlap of one outer/one inner plate]
-Just too new, the chain hasn’t worn to the chainring yet (whenever I replace the chain/casette/rings, it takes a ride or two to stop jumping/skipping and so on
It could be something else
And it could also be that the old chainring was so worn, its worn the chain too.
Use/buy/borrow a chain wear tool and see how stretched it is. If the old ring was really bad and has worn out the new chain, it’ll be obvious. Get a new chain (though could’ve worn the casette too). If the chain tool is miles off fitting the chain and it has no play in it whatsoever (and no or very little obvious wear on the little inner rollers (the bit that goes in contact with the rings) then its probably better to make the new ring ‘fit’ the partially used ring