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[Facts] Re: How would you pronounce Leofwine?
AE ligature does not come later and is not a blend. OE had seven vowels: |a| as in part, |e| as in pet, |æ| as in pat, |o| as in pot, |i| as in pit, |u| as in put, and |y|, the ü in uber and the u in Greek upsilon. Then there are the long versions of each, which are genuine long versions of the short vowels, unlike in modern English. There are dialect variations, and a lot of argument as to exactly which IPA sound is closest. but that's it broadly. Modern English has more vowel sounds but less letters.Medial f and b are pronounced |v| (as in leaves, wolves etc.), but since this is a compound of leof where the f is terminal let's stick with |f|. The eo is a dipthong pronounced similar to the vowels in modern English air (IPA /ɛə(ɹ)/), whereas LayO or LAYo would be a tripthong (IPA Leio) or disyllabic. The entire dipthong is lengthened in Leof, so it's like a drawn out pronunciation of lair without the r. The i is long like the Nintendo Wii, the final e is a short e like Eh, not ah or ey.So close to LairfwEEneh.Of course in Kent it would be said and written Liof, which is where we get the modern spelling and pronunciation "lief", a homophone of "leaf".You need to keep the final e of wine, because otherwise it reads and sounds like Leofwin, the late version of feminine Leofwyn in Wessex and Anglia. Not that a French-speaking Norman scribe would know the difference.
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