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I've done a bit of research here, but I still have some questions.

To start with, for anyone who isn't familiar with this, we can't say the brucha for lulav & etrog after completing the mitzvah, and the mitzvah is completed as soon as we gather the 4 species together and they are all right-side up, so we first pick up the Etrog upside-down, say the brucha and then turn it right-side up.

For the Etrog, The Shulchan Aruch says right-side-up is the way it grows: pitom-up, (and we should first pick it up pitom-down). And I remember being taught as a kid the Etrog first grows pitom-up and then turns pitom-down.

On the other hand,"The Second Jewish Book of Why" (page 266-267) says, etrogs grow pitom-down and growing pitom-up is a misconception that dates back to "the German Authority Jacob ben Moses Mollin (1360-1427)" who described the procedure in "Minhagay Maharil", and that it is an error in the Shulchan Aruch as well. It also cites that Rabbi Yechiel Epstein and Rabbi Israel Ben Meir Hakohen were aware that Etrogs grew pitom-down, but ruled it is a minhag (custom) now.

adult etrog

However, when I look at photos of etrogs, the young etrog-buds do grow pitom-up first: young etrog young etrog

As opposed to how a kiwi immediately hangs down: young kiwi

  • Do Rabbi Yechiel Epstein (Aruch ha-Shulchan) and Rabbi Israel Ben Meir Hakohen (the Chafetz Chaim?) actually agree they don't grow this way?

  • Does it matter at what growth-point the etrog is considered a fruit (unripe fruits are ha'adama, not ha'eitz)? or what growth-point is an etrog kosher for use? Can an etrog be too small?

  • Are there other cases where we need to know the orientation of a fruit? -note: Willow branches grow facing down but we consider the "top" of the branch to be the the end of branch pointing towards the ground. Do we consider willow branches to also grow upwards first?

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You're asking too many questions. I think the question of whether an Ethrog can be too small is a distinct question, whose answer, I assume, is that it must be a mature fruit. As for apples, I think it's irrelevant. Willow ('Aravah) may be relevant, but we do, in fact, hold it stem-down ("top"-up), just as we do with the myrtle (Hadas) and the date-palm (Lulav). Again, too many questions. –  Seth J Jul 27 '11 at 19:27
    
Also, can you cite a specific page or chapter in the "Second Jewish Book of Why"? And does that book cite specific sources for those opinions quoted? –  Seth J Jul 27 '11 at 19:28
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I think they're all (except the apple) directly related to whether the pitom grows up or down. How would we define a mature fruit? I remember reading a fruit is considered a fruit when it is recognizable as a fruit, but I'm not sure exactly where it says this. Willow - right, but what we call "top" grows towards the ground, so why is the end that we call "top" not the bottom - is there somewhere that says it also grows up-wards first? –  zaq Jul 27 '11 at 19:40
    
page 266-267, and no specific sources. –  zaq Jul 27 '11 at 19:42
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When I went to נאות קדומים, I saw plenty of mature esrogim growing with pitom facing up, though a lot of the esrogim were also facing pitom down or to the side or at some other angle. –  Fred Sep 10 '13 at 20:28
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2 Answers

The origin of this halachah is on Succah 45b where Chezkiah says in the name of R' Yermiah in the name of R' Shimon bar Yochai that we learn from the pasuk "Atzei Shittim Omdim" ('Acacia wood standing' there is an apparently extra word 'standing') That for every mitzvah in the Torah a man does not fulfill them except in the way that they grow. Rashi explains that this means that the part that comes from the bottom goes down and the part that goes up is on top.

The stem of the plant, the part that is attached to the tree, is the part that leads toward the ground, whichever way that particular fruit or branch grows on the tree. So, for example, when you hold the arbah minim the parts of the esrog, lulav, haddasim and aravaos that are attached to the tree are the parts we hold down.

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I think this is correct, but Rashi doesn't really spell out that no matter how it actually grows (pitom up or down) the stem is the bottom because that's where it attaches to the plant. Rashi could just mean that the part that is the bottom (as it grows) is the bottom, and the part that goes upwards (as it grows) is up. –  zaq Aug 7 '11 at 20:56
    
I just want to clarify, that it is actually irrelevant which direction the etrog hangs on the plant, the part that connects to the ground is the bottom (even if it is on top when it grows). –  zaq Aug 8 '11 at 13:25
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http://en.wikipedia.org/wiki/Four_Species

The 4 species must be placed in the direction in which they grew. (For the etrog, this means that the stem end should be on the bottom and the blossom end on top; this is the direction in which the etrog begins to grow, though as it matures on the tree it usually hangs in the opposite direction.)

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Good find, but where do they get that from? If it's from the Shulchan-Aruch, or a similar source, then this could just be the "misconception. –  zaq Aug 2 '11 at 14:29
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@zaq My Rov said exactly the same point without Wikipedia. –  Avrohom Yitzchok Oct 6 '12 at 20:37
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