Both monophthongs and diphthongs underwent radical changes during the Middle English period.
a) Monophthongs.
OE [a, o, ō, u, ū, e, ē, i, ī] remained more or less unchanged in Middle English, while OE [ā, æ, æ, y, y, å] changed radically.
1.OE [ā] > ME [ō] everywhere but in the northern dialect. This new [ō] was of much more open nature than the OE [ō] preserved in Middle English. In order to distinguish the two kinds of [ō] we shall use the symbol ọ to denote the open [ō] and the symbol ọ for the close [ō]. In Middle English manuscripts the two types of [ō] were mostly represented by the same symbols: o in open syllables and oo in closed ones. Later the two [ō]’s were distinguished not only in sound but in spelling as well, [ọ] being as a rule represented by the digraph oo, and [ọ] by the digraph oa in closed syllables and the letter o in open ones.
E.g. OE bāt, āc, nā > ME boot, ook, no (E boat, ok, no).
OE ™ōd, sōna > ME good, sone (E good, soon).
Note. ME [ō] from [o] in open syllables was also of an open nature and mostly coincided with [ọ] < OE [ā]. Therefore we find the same way of representation of ME [ọ] in E hope (< OE hopa) and E stone (< OE stān).
2.OE [æ] > ME [ę] (more open than [ẹ] < OE [ē]). Thus in Middle English there were two types of long [ē]: an open [ę] and a close [ẹ]. In Middle English manuscripts they were often expressed in the same way: a single letter e in open syllables and a double ee in closed ones. Later these different sounds were distinguished also in writing: [ę] was represented by the digraph ea and [ẹ] by the digraph ee.
E.g. OE sæ, mæl > ME se, meel (E sea, meal).
OE fēlan, fēt > ME felen, feet (E feel, feet).
Note. The sound [ę] developed in ME also as a result of the lengthening of [e] in open syllables. Thus, OE etan, mete > ME ēten, mēte (E eat, meat).
3.OE [æ] > ME [a].
E.g. æt, þæt, dæ™ > ME at, that, day.
4.OE [å] > ME [o] only in West Midland. In all other dialects OE [å] > ME [a].
ME long, mon, long (West Midland)
E.g. land, mån, lån™
ME land, man, lang (Other dialects) (E land, man, long)
In most cases the Modern English form is based on that of the Eastern dialects. Only before -ng- forms with o predominate.
E.g. long, strong, song.
i, ī in the North-East
5.OE y, y remained unchanged in the South-West (written u, ui)
e, ē in the South-East (Kent)
N.-E. hill, fīr, (E hill, fire)
E.g. hyll, fyr S.-W. hull, fuir
S.-E. hell, fēr
In the majority of cases Modern English has forms with [ǐ]. But sometimes the influence of other dialects is felt. In the word busy, for instance, the spelling reflects the influence of the Western dialects. The same is true about the verb to build. The pronunciation of the verb to bury is due to South-East dialects, while the spelling is of Western origin.
b) Old Diphthongs.
All the Old English diphthongs were monophthongized as early as the 11-th century, losing their second elements.
1.OE ēa and ea whose first element sounded [æ] (long and short) were reduced to [æ] (long and short) and developed accordingly.
OE ēa > ME ę, e.g. OE ēast, strēam > ME eest, streem (E east, stream).
OE ea > ME a, e.g. OE earm, heard > ME arm, hard.
2.OE ēo and eo gradually became ẹ and e respectively.
OE ēo > ME ẹ, e.g. OE dēop, sēon > ME deep, see (E deep, see).
OE eo > ME e, e.g. OE feor, deorc > ME fer, derk (E far, dark).
c) New Diphthongs.
As a result of the vocalization of [j] and [w] new diphthongs were formed whose second element was either [i] (written i, y) or [u] (mostly written w).
1. [ei], OE we™, se™l > ME wey, seil (E way, sail).
2. [ai], OE dæ™ , fæ™r > ME day, fair (E day, fair).
3. [au], OE sa™u, clawe > ME saw(e), claw(e) (E saw, claw).
4. [ou], OE bo™a, snāw > ME bowe, snowe (E bow, snow).
5. [eu], OE dēaw, nēowe > ME dew, newe (E dew, new).
Note. Some linguists are of the opinion that the French long labial [ǖ] was replaced by the diphthong [eu] in those areas where OE y [ü] was not preserved, i.e. everywhere but the South-West. E.g. fruit was pronounced [freut] in ME, deu – [deu]. This is the reason why ME trewe (< OE trēowe) has come to be written true and why the pronunciation of dew and due is the same.
Besides the above-mentioned diphthongs it is necessary to mention the diphthong [oi] mostly found in French borrowings like poynt (E point), poison, vois (E voice), etc.
The Middle English Sounds and Letters
(London Dialect of the Second Half of the 14-th Century)