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I can think of this sentence -

(Don't touch that) That is my brother's company's CEO's son's dog's toy. - I can still come up with many more apostrophes! ;)

Is there any rule that talks about the number of apostrophe to be used in a sentence? This sentence is hypothetical but does such sentence with many apostrophes exist? Is there any context where more than two or three apostrophes cannot be avoided?

If there is no rule -

The sentence is understandable the way I wrote. But then, if there's no rule, how do I say the above sentence without apostrophe, how do I say? I am afraid, you have to include many of them! Or else, you'll have to break the sentence. :)

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That is my brother's dog toy is enough confusing I think. –  Santi Santichaivekin May 23 at 12:36
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Syntactically, there's no constraint on the number of ownership relationships, because of recursion. Pragmatically, you might want to break it up. - You know my brother's company? The CEO's son, that's his dog's toy. –  jimsug May 23 at 12:38
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@MaulikV This reminds me of "The rat the cat the dog chased killed ate the malt." Though they might not be obviously related, both of them remind me of something people can construct but do not normally think, so naturally it's rare that we will hear them. –  Damkerng T. May 23 at 12:53
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How many words are allowed in a sentence? How many preposition phrases can be strung one after another? How many conjunctions can we use in a single sentence? When it comes to such questions, the English language has no strict limits, but common sense tells us when too many is too many, and it's time to do some rewriting. –  J.R. May 23 at 15:38
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As for a suggested rewrite, here's mine: Don't touch that! That is Fido's toy. –  J.R. May 23 at 15:40

5 Answers 5

There are no rules limiting the number of instances of such punctuation, and likewise there is no limit to the levels of possession that can be attributed to something. But as you observe, both the repetitive usage and the denseness of the nested genitive make it difficult to parse, and something to be avoided.

But we rarely ever trace more than about three degrees of separation in this way, unless for literary or humorous effect.

I am your father's brother's nephew's cousin's former roommate

As such there is no single best way to rephrase. I would retain apostrophes where you want to emphasize the relationship and replace the others with some combination of prepositional phrases, noun adjuncts, and verbs of possession or association. The idea would probably be better split up into multiple clauses or sentences as well.

My brother's CEO brought his son's dog. That is the dog's toy.
That toy belongs to the dog of the son of the CEO of my brother's company.
That's a dog toy, for the dog of the son of my brother's company CEO.

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I knew Spaceballs was going to make an entrance as soon as I read the first sentence... –  phyrfox May 23 at 19:14

No, there is no rule in English that says you cannot have more than 3 apostrophes in a sentence or any such number. Just as there is no rule that says you cannot say "of" more than some number of times, or you cannot have more than so-many distinct clauses, etc etc. OF COURSE it is possible to write a sentence that obeys all the regular rules of grammar, but which is difficult to understand, confusing, or awkward. If you see writing a sentence as a contest where you are trying to make the sentence difficult to read while still technically obeying all the rules, you can win every time. Just like, traffic laws are supposed to make driving safer. Is it possible to drive in a way that unnecessarily endangers the life of yourself and others while still technically obeying all the traffic laws? Of course.

The sentence you give isn't really particularly difficult to understand. If I was reading a book and in the middle of a discussion about your brother and the CEO of his company this sentence came up, would it strike me as odd or would I just read on through? Hard to say.

In any case, such a sentence is unlikely to come up in practice. You need all the apostrophe's because you are stringing together a series of identifiers to describe just what dog you are talking about. But in a real paragraph, you probably would not suddenly want to introduce this dog and his toy out of the blue like that and find a need to explain who this dog was. Or that you would be talking about multiple dogs belonging to multiple sons of multiple people all of who are CEOs, so that you need to clarify just which one you are referring to. More likely is that you would be introducing each of the players one at a time. "My brother works for a big electronics company. The other day he went to a meeting that the CEO had called to discuss ... The CEO began by taking an animal's chew toy out of his briefcase. 'See that toy?', he said. That belongs to my son's dog. Our products should be like that toy because ..."

If such a sentence really did come up, you could rework it by replacing the apostrophes with words to describe the relationship. Like, "That toy belongs to the dog owned by the son of the CEO of the company that my brother works for."

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There is no rule. As for how to say it while still sounding like a normal human being, you would have to identify which/who is/are the necessary subject of the point you are trying to get across.

That is my brother's company's CEO's son's dog's toy.

The necessary subjects in the above sentences are: The brother, CEO, CEO's son and his dog. The company is not needed because it makes no difference to the point you are trying to get across. The focus of the statement is not on the company but rather, on the toy belonging to the son of a CEO.

That is a dog toy, belonging to the son of my brother's CEO.

You would have to accept one fact: Nothing belongs to a pet. Everything is allowed by it's master. So, in reality, the toy really belongs to the CEO's son, not the dog. Of course, many people would say "Oh, that belongs to my dog!" They are not wrong. However, in the context of your statement, the severity of touching the dog toy is not because it actually belongs to the dog, but to the son of the CEO of your brother.

Another statement from choster's answer,

I am your father's brother's nephew's cousin's former room mate

In this statement, I assume the father only has one brother because it does not state elder or younger.

A nephew is the son of a sibling. Your father's brother is called an uncle. And your uncle's nephew is your father's son which would be you! So, basically, the whole statement can be reduced to,

I am your cousin's former room mate.

From my understanding. the key to writing and/or speaking sound statements is rooted in identifying the key subjects of the point you are trying to get across. A CEO holds a good, or rather, a very strong weight that the word company is not needed in the context of your statement.

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If Joe has an uncle (by blood) Fred, he will be one of Fred's nephews, but not necessarily the only one. If Fred's wife Ellen has a sister Rose, and Rose has a son Larry, then Larry would be Fred's nephew, and could thus be described as "Joe's father's brother's nephew", but would have no relation to Joe. –  supercat Jul 23 at 21:12
    
@supercat Sigh. Your explanation is out of context to the statemebt given. Anyway, this is old. Goodbye :). –  Zoe Jul 24 at 0:05

I'm surprised that nobody's mentioned this, but you can substitute of for the possessive apostrophe-s, if you reverse the word order:

That is my brother's company's CEO's son's dog's toy

becomes

That is the toy of the dog of the son of the CEO of the company of my brother.

It has no apostrophes, but I don't think that in any way improves intelligibility.

Also you could have gotten another apostrophe in there, by contracting "That is":

That's my brother's company's CEO's son's dog's toy.

Of course, if we're trying to maximize apostrophes, cunning word choice and dialect can help:

That's m'aunt's company's CEO's son's wife's 'cello.

There's no rule against doing that, it's just a crime against good taste.

Edited to add: In addition to the good alternatives posted by others, I'll add, "That's the dog-toy of the son of my brother's company's CEO."

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Like you say, it's correct, but very implausible. I cannot think of a situation where that would even get used, even though its correct.

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I edited: One more thing, if I want to say the above sentence without apostrophe, how do I say? I am afraid, you have to include many of them! –  Maulik V May 23 at 12:18
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@MaulikV Avoiding apostrophes is clearly a bad idea, but maybe you could say something like: "Do not touch that—it is the toy for my dog that belongs to the son of the CEO at the company where my brother works!" –  snailplane May 23 at 13:53
    
@snailplane my dog? It's ceo's son's. Oops I used three again –  Maulik V May 23 at 15:31
    
@MaulikV Yeah, you are right. In trying to unnaturally avoid apostrophe use, I confused myself. It should have said the rather than my. –  snailplane May 23 at 22:18

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