When did the Nachash have relations with Chavah?

Rashi: This is when it enticed her. "Ha'Nachash Hishi'ani" is an expression of Nisu'in.

Maharal: The Nachash wanted to kill Adam and marry Chavah. It had improper Bi'ah with her - this connection put in her filth and abomination.

Daf Al ha'Daf citing Yisrael Saba (66 p.805): How could Chavah believe that via eating from Eitz ha'Da'as, she will be like Elokim?! Therefore, he had Bi'ah with her, and via desire for adultery, a spirit of folly entered her, and she came to deny.

What filth did the Nachash cast into Chavah?

Etz Yosef citing Nefesh ha'Chayim: It brought a great mixture into her deeds - sometimes good and sometimes evil. Also the good deeds, it is almost impossible to be totally pure without some ulterior motive. Also bad deeds, often a good intent is mixed in. At Sinai, this filth departed.

Why were Yisrael cleansed of the filth on Sinai?

Rashi: They were cleansed of all blemishes, like the Midrash (Mechilta Yisro 9) says.

Rav Elyashiv: Nochrim prefer [Bi'ah with] Jewish animals over their own wives. The Nachash inserted filth in Chavah; the filth left Yisrael, but not the Nochrim (Avodah Zarah 22b). This implies that the filth left even Jewish animals! (NOTE: What is the source that filth entered animals? And what is the source that it left at Sinai? Do Nochrim desire Bi'ah only with animals descended from Jewish animals at Sinai, but not with what Jews buy from Nochrim?! Further, Nochrim do not have Bi'ah with their own animals because this sterilizes or weakens them (ibid.). If not, they would prefer them over their own wives! - PF)

Maharal: The Nachash put filth into Chavah via Bi'ah (connection] with her. At Sinai, Yisrael connected to Hash-m!

What was the question 'what is with converts?'

Rashi: They did not stand on Sinai - when did their filth depart?

What is the significance that their Mazel stood on Sinai?

Rashi: This was Metaher and Mekadesh them, like Yisrael.

Daf Al ha'Daf: Ohr ha'Chayim (Devarim 33:3) says that the filth did not leave converts. Toras Yakov brings from R. Akiva Eiger (and the Ger Tzedek of Vilna said similarly) that when Hash-m offered the Torah to all the nations, a minority wanted it - these are the converts in all generations. A minority of Yisrael did not want it - these are the apostates. Sha'arei Simchah (Yisro) says that apostates hate Yisrael more than Nochrim do (Toras Moshe Shofetim), for they are from those who did not want the Torah. However, Yad Ohr ha'Chayim (Kavei Or 14) brings from the Zohar like Ohr ha'Chayim said! This requires investigation. (NOTE: Perhaps the Zohar means that a trace of the filth remained, and also our Gemara means that almost all of it departed. - PF)

Maharsha: "Asher Yeshno Po ha'Yom" are those who stood on Sinai. "Asher Einenu Po Imanu ha'Yom" are future generations and those who will convert later (Shevu'os 39a). For Yisrael, we can say that their Neshamos, which are wrapped in Tzeror ha'Chayim, were there. We cannot say so for converts. Rather, their Mazal was there.

Why must we say that Rav Ashi argues with R. Aba bar Kahana [who says that there was no filth in the Shevatim]? Perhaps Rav Aba teaches that at Sinai, the filth left the Erev Rav and others who converted before Sinai!

Iyun Yakov: This is difficult. (NOTE: 'Yisrael stood on Sinai' implies Bnei Yisrael, and not just converts! - PF)

Daf Al ha'Daf citing Shelal David (Mishpatim): According to R. Aba bar Kahana, how did filth leave converts? He agrees that filth departed at Sinai, just he holds that it departed already from the Shevatim, but it returned in Egypt when they descended to the 49th level of Tum'ah. "V'Ger Lo Silchatz" - do not tell him 'you ate Neveilos, and now you learn Torah?!' (Bava Metzi'a 58b). Do not say, our filth ceased from the Avos, but the converts filth remained. "Ki Atah Yadata Es Nefesh ha'Ger Ki Gerim Heyisem b'Eretz Mitzrayim" - just like your filth [returned in Egypt, and] departed at Sinai, his filth departed at Sinai.

Daf Al ha'Daf: A case occurred in which a Shiduch was made, and afterwards the Chasan's grandfather became a Mumar. Noda bi'Yhudah (1 YD 69) learned from R. Aba that this is reason to retract. Just like Terach's filth was found three generations later in Esav, the grandfather's sin can affect the Chasan's children.