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Romanic phonological evolution



Hey all,

I'm guessing this is a fairly obvious question, but I feel the need to
ask it for the sake of my own understanding. Also I intend to be
rather compulsively adherent to certain rules in the process of
designing my first conlang (obviously, a Romance conlang)... in other
words, I want this language to be convincingly realistic, so I don't
want to make too many more radical changes than are expected.

Here goes--

I know a lot about historical linguistics and phonological changes,
and I even know a lot about the evolution of Classical Latin to
Vulgar, but to be honest, my expertise is more deeply rooted in the
modern Romance languages, especially Spanish. I know that phonological
changes are sweeping, contextual, and consequently fairly easily
traceable. But even in the instances in which they supposedly "always"
occur, are there ever more-than-minute exceptions to those rules? For
instance, might there be an instance in a Western Romance language
where, though most voiceless stops became voiced, there are a cluster
of words where, for some reason, "t" was expected to become "d" but
somehow didn't? Or maybe we simply can't reconcile the way certain
minute words and particles evolved, like the modern equivalents to
prepositions "de" and "ad?", in comparison to the "rules" by which
these languages otherwise evolved? I realize this is a pretty general
question, but for some reason, this one dilemma seems to be holding up
my creative processes.

To shed some light, I'm a mathematician (hence, compulsively
analytical), and getting the jump on conlanging a little later in life
than what I'm gathering is the obvious age (i.e., I'm not in high
school), so perhaps I feel a bit inclined to really prove myself with
this first outing. :-P

Big thanks for any insights on the matter.

Cheers.

-Mark