Question #1: What did the נחש do that warranted the description ערום (shrewd, cunning, naked)?
והנחש היה ערום, we must assume that the serpent per chance had already eaten from the tree of knowledge, as the warning not to eat from it was issued not only to man.
The matter becomes clearer, however, when one examines what the serpent intended to achieve with the words אף כי אמר אלוקים לא תאכלו מכל עץ הגן, "even though G'd said not to eat from any of the trees of the garden." Since we know that these words were totally untrue, we would have considered the serpent as feeble-minded. The Torah therefore has to preface the account by pointing out that these words were carefully calculated, that the serpent was exceedingly sly. Any creature which is not exceedingly sly would most certainly not have succeeded in seducing a G'd-fearing woman such as Eve.
Question #2: How did the snake ultimately convince Chava to eat from the Etz HaDaat?
והנחש. יש אומרים כי האש' הית' מבינה ויודעת ל' החיות. ויפרשו ויאמר הנחש ברמיז'. ואחרים אמרו שהוא שטן ואיך לא יראו סוף הפרש' כי איך ילך השטן על גחון ואיך יאכל עפר.
And it said to the woman. Some say that Chavah understood the gestures of the animals. According to Rav Sadyah Gaon, however, whenever speech is ascribed to an animal it is actually an angel that is speaking on its behalf. Alternatively, it is possible that these verses are to be taken literally, since it is no more difficult for Hashem to give intelligence to a serpent than to human beings.
The serpent concentrated on three subjects and by combining them achieved its purpose.
1) The serpent told Eve that by not eating from the tree of knowledge she would remain for all intents and purposes as if she had not eaten either from any of the other trees. The serpent indicated that the fruits of the other trees were totally inferior when compared to the fruit of the tree of knowledge.
2) The serpent pretended to teach Eve a halachah, thus creating the impression that it was very knowledgeable and on G'd's wavelength. It told Eve that G'd had first planted the tree of knowledge and had then used its shoots to plant all the other trees in the garden. This was part of the seduction. Once the original tree is out of bounds the other trees are automatically forbidden inasmuch as they are "earthed" branches of the original tree
3) The word אף referred to the fact that G'd had not commanded Eve anything directly, He had only commanded her husband. The serpent said that it was a witness to the fact that G'd had indeed forbidden the eating of the fruit of any of the trees...The serpent reasoned that since there were only two witnesses, i.e. Adam and the serpent, Adam having testified to a single tree being forbidden whereas the serpent testified that all trees were forbidden the halachah should be based on the school of Shammai, i.e. the testimony was void, and as a result Eve could not be held culpable for eating from the tree of knowledge.
Question #3: Did the Snake really speak to Chava?
‘אף כי אמר וגו And although he saw them eating of the other fruits yet he entered into a long conversation with her so that she should answer him, and so that he might then have an opportunity to talk about that particular tree.
Question #4: Did Hashem really command Adam & Chava against "touching" the Etz HaDa'at?
“Did God really say: You shall not eat of any tree of the garden?”: There is a big question in this matter: If the woman added the command of "do not touch" by herself; behold, she knew the truth that God did not command about the touching. And if so, how was the woman seduced by these empty words, saying that in the same way as there is no death penalty from touching, so too is there no death penalty from eating?
From a quick [survey], it appears that it can be explained that the woman did not hear the commandment from the mouth of the Mighty One, but rather from the mouth of her husband...And the man saw in his [own] intellect to make a fence and to add upon the command; to forbid even touching to his wife, so that she should not come to eating. And Chava reasoned that everything he said to her was from the Mighty One.
Therefore, this mistake came to her; as the snake found it, [in order] to deceive her. And with this [explanation], we do not need the explanation of Rashi, who explained that is for the [following] reason that the snake did not come to the first man (Adam) - because women are weak-willed and are easy to seduce. As without this, there is no difficulty; as behold, the snake wanted to prove from touching, that there is no death penalty with eating. And with the first man, he would not have been able to prove anything, since Adam knew the truth: that God did not command about the touching and that he added it on his own.