(Mishnah): If one separated cucumbers as Terumah and then found them to be bitter (and perhaps not considered food); or if he separated melon and found it to be rotten, they are Terumah, but he should separate again.

If one separated a barrel of wine as Terumah and then found it to be vinegar, if he knows that it was vinegar before he separated it, it is not Terumah. If it became vinegar only after he separated it, it is Terumah. If he is unsure, it is Terumah, but he must separate again. The first Terumah cannot prohibit a mixture alone and one is not obligated in adding a fifth (if a person ate it unintentionally). The same applies to the second Terumah.

If one of them fell into Chulin, it doesn't make it prohibited. If the other one fell elsewhere, it doesn't prohibit that mixture. If they both fell into the same place, it becomes prohibited according to the smaller of them.

Question: 'If one separated cucumbers etc.' - melon that is found to be rotten is understandable, but if cucumbers are found to be bitter, weren't they always bitter?

Answer (R. Yochanan): (Since there are bitter cucumbers which are not edible at all and some which are only mildly bitter) the Chachamim viewed them as doubtful food (and therefore they are Terumah, but he must separate again).

Question (R. Yona): Did they view it as doubtful food in all ways? Do we say that it can contract Tumas Ochlin (like food) and it is burned in a state of Tumah (like Terumah Temeyah), and if a non-Kohen would eat it he would need to pay an extra fifth and if it was Maaser Sheni, one would receive lashes for eating it outside of the walls of Yerushalayim; and as to whether it is valid to use for Eruvei Techumin...? Do we say that we must be stringent for Eruvei Techumin and rule that it doesn't permit walking any further...? (The Gemara doesn't answer this question.)

Question: There (in Maseches Shevuos) R. Yochanan said that if a loaf of bread might have become Tamei in a private domain, it is Tamei. If it then touched something in a public domain, it is Tamei (and we don't view it as a doubt to allow us to be lenient in the public domain, since it certainly touched there and the doubt only took place in the private domain). Here, in the case of the cucumbers found to be bitter (that became Tamei in a private domain) there are two doubts (as it is also doubtful whether it is still considered food, so when touched something in a public domain, that thing remains Tahor).

(Baraisa citing R. Yosi): (Disagreeing with our Mishnah) only the inner part of the cucumbers are bitter so he must only separate that part again.

Question (R. Binyamin bar Levi): How could the Chachamim disagree over something that can be clarified (as the outer part could simply be tasted)? Rather, they disagreed over whether the outer part was bitter enough to be considered inedible.

(Tosefta): If he separated a barrel as Terumah and found it to have been left uncovered overnight or a melon and found it to have been nibbled (causing concern that a snake put his venom into them), they are Terumah, but he must separate again.

(R. Yudan bar Pazi/R. Shimon citing R. Yehoshua ben Levi): They only discussed when it was found to have been nibbled, but if it had been so originally, the Terumah is invalid.

Question (R. Yaakov Dromai to R. Yosi): This should seemingly only be true if he saw the snake nibbling; (otherwise, it is a doubt, and he should separate again)...?

Answer (R. Yosi): Even in that case, does he know that the snake released his venom into it?

Question (Chevraya to R. Yosi): How is this case different to when one separated Tameh for Tahor (where the Mishnah taught earlier in Perek 2 Mishnah 1 that it is valid Terumah)?

Answer (R. Yosi): It's only the Tumah that prevents it being eaten, but here, it is completely inedible.

(R. Yaakov bar Acha citing R. Yochanan): The Halacha follows Rebbi (who said that wine and vinegar are two species).

(R. Chiya citing R. Yochanan): Our Mishnah is the opinion of Rebbi (as it indicates that if one separated from vinegar for wine, it is not Terumah).

Question (R. Ba bar Kohen to R. Yosi): Didn't R. Chiya cite R. Yochanan as saying that in a disagreement between Rebbi and his collegues, the Halacha follows Rebbi. And R. Yona said that this even applies in a disagreement between Rebbi and R. Elazar (so why must it be said here)?

(R. Yosi to R. Ba): Since a Tosefta teaches that R. Yishmael b'R. Yosi disagrees with Rebbi in the name of his father (and says that wine and vinegar are one species) and R. Yosi (the Amora) has said in the name of R. Yochanan that the Halacha follows R. Yosi over his colleagues, you shouldn't think that that even applies when R. Yosi disagrees with Rebbi.

(R. Zeira/ R. Yaakov bar Idi citing R. Yochanan): When R. Meir and R. Shimon disagree, the Halacha follows R. Shimon. When R. Shimon and R. Yehuda disagree, the Halacha follows R. Yehuda. And it goes without saying that if R. Meir and R. Yehuda disagree, the Halacha follows R. Yehuda.

(R. Ba/ R. Yaakov bar Idi citing R. Yonasan): When R. Meir and R. Shimon disagree, the Halacha follows R. Shimon. And it goes without saying that if R. Meir and R. Yehuda disagree, the Halacha follows R. Yehuda. From this we can conclude that if R. Shimon and R. Yehuda disagree, the Halacha follows R. Yehuda.

(In a case of doubt when he must separate Terumah again) what must be done? He gives both Terumos to the Kohen and the Kohen pays him the value of one of them. Which one? The larger or the smaller one? (The second one will be smaller since it is taken from the produce that is now smaller because it is without the first Terumah.)

Answer: Since we are lenient when both of them fell into less than 100 parts Chulin, that it prohibits the mixture according to the smaller one, this shows that the smaller one is given to the Kohen without charge and the Kohen must pay for the larger one.