What is the definition of "Ashmores ha'Boker"?
Rashi: The night is divided into three watches (each comprising four hours), when three groups (Mishmaros) 1 of Mal'achei Shareis sing Shirah one after the other. It was at the beginning of the morning watch - the final one - that Hashem began to switch from the salvation of Yisrael to the drowning of the Egyptians.
Rashi: Which explains why the Torah uses the word "Ashmores" (and Onkelos - 'Matras'). Gur Aryeh - The words "Ashmores" and "Mishmar" share the root Shin-Mem-Resh, meaning 'to guard.' The members of each shift, guard and preserve their order and sequence.
What are the connotations of the word "va'Yashkef"?
Rashi: It means that Hashem looked down upon them in order to destroy them. 1
See 14:24:2.1:1 below .
Why does the Torah again refer to the Pillars of Fire and of Cloud?
Rashi: Because they worked in conjunction to create havoc among the Egyptians. The former turned the congealed water into mud, and the latter then boiled the mud. The boiling mud burned the hoofs off the horses' feet (causing them to go wild [and the wheels off the chariots, causing the chariots to drag, their riders being hurled around until their bones came apart]). 1
Targum Yonasan: The Pillar of Fire shot burning coals at the Egyptians, and the Pillar of Cloud, hail-stones.
See also commentaries on the next Pasuk (14:25).
What are the connotations of "va'Yahom"?
Rashi #1: It means that Hashem confused them, causing them to lose their common sense. 1
Rashi #2 (citing Pirkei d'R. Eliezer ben R. Yossi ha'Gelili), Rashbam: It means that Hashem caused them to hear terrifying noises. 2
Targum Onkelos and Targum Yonasan: It means that Hashem caused them to go crazy.
Seforno: It means that they were smitten with all kinds of illnesses. 3
Hence, in 14:27, the Pasuk describes how they ran towards the oncoming water, instead of running away from it. (See Rashi there; refer also to 14:25:1:2 .)
Rashi: As in Shmuel I 7:10. These were caused by hail (presumably with reference to the Pillar of Cloud [refer to 14:24:3:2]), which contained fire (caused by the Pillar of Fire).
Seforno: Which the Torah refers to as "Madvei Mitzrayim" (Devarim 7:14).
QUESTIONS ON RASHI
Rashi writes: "Va'Yashkef - He gazed upon them, [i.e.] He turned upon them, to destroy them." Why explain this way?
Mizrachi, Gur Aryeh: All instances of the term "va'Yashkef" in Scripture have negative connotations (Rashi to Bereishis 18:16). 1
The only exception is "Hashkifah.. u'Varech Es Amecha, Es Yisrael" (Devarim 26:15), in the merit of the Mitzvos of gifts to the poor.
Rashi writes: "The pillar of cloud went down and made [the sea-bed] like mud." Why was this necessary? The water of the sea itself could have accomplished the same?
Gur Aryeh: Sea-water is crystal-clear; it would not have formed mud. The cloud, which was itself thick and dense, mixed with the earth to form thick mud.
