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There are several features of Akkadian that set it apart from other Semitic languages. One such feature is the assumption of seven alefs that descended from Proto-Semitic phonemes, *ʔ, *h, *ʕ, *ɣ, *ħ, and sometimes *w and *j. The standard account is that they merged before being lost in nearly every environment. Additionally, ʔ3-5 interact with the low-back vowel, [a], producing [e]. Two other issues regarding the shift from [a] to [e] is which environments [e] surfaces in to be reanalyzed, and the fact that there are several roots that have [e] and no apparent conditioning environment. In this article I provide a solution to these issues clarifying the conditioning environments obscured by Akkadian orthography and Semitic derivational morphology. I show that voicing assimilation alone is responsible for the different outcomes of *ħ and *ʕ, which have the same distribution. This assimilation has parallels in non-guttural roots such as *√ntn, which becomes √ndn in Akkadian. Whether *ʕ and *ħ surface as <∅> or <ḫ> depends less on the underlying form than on assimilation to the voicing value of the adjacent consonant radical. With this analysis, there is no reason left to reject Kowenburg’s theory (2006) that gutturals became glides which cause raising to [e], with the slight amendment that it is the voiced variant *ʕ alone which becomes a glide.