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I think these are correct but would appreciate help with the parsing......

5a. To fail to understand is comprehended by diplomats (6) - CLOSED? It looks like LOSE (Fail) in CD (Corps Diplomatique) but if that's right I can't see a definition.

12d. Battle site partially cleared in old city for ugly skyscraper (11) - MONSTROSITY

14d. Roughly redesigned crease out of chalk (10) - CRETACEOUS (Of Chalk) I thought it was an anagram of CREASE OUT but I'm a C short, so...

14 the c comes from roughly (circa)

Battle - Mons + site partly in Troy - old city - Mons tro sit y?

Hi again Brendan,
To, as in a door pushed to = closed
Mons + Tro(sit[e])y
Roughly = c, circa

If a door is closed it is "to" as in "pull the door to"? To is the definition?

Excellent, many thanks Ab, Ginge and Jazzgirl.