One Apostrophe Replacing Letters at 2 Sites in a Word

There are a few words where a single apostrophe replaces letters at two different locations in a word. The one that comes to mind is Lil’ . As in Lil’ Kim, and many other uses. Less frequently you will see it Li’l . As in Li’l Abner. The apostrophe is replacing two T’s in the middle, and the silent E at the end.

Is there a rule on proper placement of the apostrophe, or is this just a case-by-case situation where tradition governs proper form?

And maybe if Samclem reads this, he can tell us whether Lil’ is more common now than in the past.

Other words:
won’t
shan’t
'n vs. ‘n’

A related thread that didn’t really address my question:

Double Contractions

Fo’cs’l, the most forward living quarters in a ship, was originally forecastle. Several seagoing words are compressed, but right now I can’t think of any more with more than one letter-replacing apostrophes.

A’kNo’t

My sense is that the use in this case is entirely due to convention. The contractions are, obviously, “officially” designated. “Li’l” on the other hand is just a colloquial usage, so I don’t think it really matters where the apostrophe goes. I also agree that “Li’l” was more popular in the past than “Lil’”–but either seems “correct.”

I’ve never seen Lil’ – and submit that Li’l is actually representing a glottal stop, not a /t/, in one pronunciation of little, as in some dialectal renditions of bottle.

Ask Nott beat me to “foc’s’l” as a two-apostrophe word, and of course the man in the foc’s’l may very well be the bo’s’n (sometimes bosun), which is a standardized contraction of boatswain.

Double-apostrophization is common in a number of colloquial contractions. What comes quickly to mind is I’d’ve, for “I would have.” I do remember seeing one solitary writer use wou’dn’t and cou’dn’t, apparently simply to pick up on the unsounded L – but that’s hardly common; in fact, I’ll bet that nothing but the complete OED lists it.

On a similiar vein, is it considered “proper” usage to form a contraction from more than two words? For example, in spoken conversation I normally contract could not have to couldn’t’ve. Would that construct be considered valid as anything other than an attempt to write in dialect?

As an aside, a humerous example that I thought up involves the phrase they are not. You normally see they are contracted to they’re, and are not contracted to aren’t, but I doubt that anyone would every say (much less write), they’ren’t.

Is “boss” a further contraction of “bo’s’n”/“boatswain”?

No, boss appears to come from the Dutch baas, meaning master.

BTW, the Random House unabridged lists a three-apostrophe fo’c’s’le as the main entry.