Some English prepositions can be used either with a nounphrase complement or without it if the context permits:
[1]  a.  Open the gate and walk through it 
b.  Open the gate and walk through. 

[2]  a.  After a while we went back inside the house. 
b.  After a while we went back inside. 
Others, like of and into, strictly require a nounphrase complement and cannot be used grammatically without one:
[3]  a.  She asked for dihydrocodeine, but I had never heard of it. 
b.  *She asked for dihydrocodeine, but I had never heard of. 

[4]  a.  We went back to the car and got into it. 
b.  *We went back to the car and got into. 
I’ll refer to the latter kind of prepositions as strictly transitive. Consider now the question stated in [5].
[5]  Is there a grammatical English sentence containing a sequence of three consecutive occurrences of a single strictly transitive preposition? 
You might think that this question can be immediately answered in the negative on the grounds that the next word after a strictly transitive preposition would have to be the beginning of a noun phrase and noun phrases don’t begin with prepositions. But not so fast: English syntax is much trickier than that. For one thing, the complement of a preposition doesn’t have to immediately follow it, but can be displaced in at least three ways.
First, there are prepositional passives like [6b], where what is understood as the complement of a preposition (as in [6a]) is in grammatical terms the subject of the clause, and thus separated from the preposition:
[6]  a.  People seldom speak of this. 
b.  This is seldom spoken of. 
Grammarians speak of such prepositions as stranded. Because of what are often called ‘subject raising’ constructions, the subject can appear arbitrarily far away from the stranded preposition:
[7]  This seems to have turned out under the circumstances to have been only very seldom spoken of. 
Second, items like interrogative or relative words or phrases can be displaced an arbitrary distance to the beginning of a clause. This is the most common way in which a preposition can be stranded. Notice that these two sentences are both grammatical, and are synonymous (though while the first is normal in style, the second is rather formal and pompous):
[8]  a.  Which regulation do you think the committee imagines the provost’s action might have been in violation of? 
b.  Of which regulation do you think the committee imagines the provost’s action might have been in violation? 
In both of these the preposition of is understood to have which regulation as its complement. Notice that in [8b] the construction involved allows the strictly transitive preposition of to be the first word in its clause.
Third, phrases can also be displaced toward the end of the clause, yielding a different way in which a strictly transitive preposition may fail to be immediately followed by its complement, as when a parenthetical is inserted after a preposition:
[9]  It was a painting of, or perhaps I should say a painting apparently intended to vaguely suggest, a cornfield in summer. 
Thus in order to settle the question in [5] it will be necessary to ensure that no facts of this sort can interact to create a way in which three transitive prepositions could become adjacent. It is not just a matter of which words are allowed to be adjacent to which other words: the interactions of the many different syntactic constructions in English are not necessarily going to be easy to foresee.
What [5] asks is whether some combination of grammatical configurations can permit a sentence to contain a sequence like of of of or into into into. It seems intuitively unlikely. But can we prove that it is impossible?
There are systematic computational ways of answering some kinds of questions about sentences in languages. The great majority of the relevant work has been based on systems of rules that Post (1943) originally called production systems, and computer scientists often call rewriting systems, and linguists call generative grammars. Basically they are sets of rules for nondeterministic random construction of abstract structures such as strings or trees.
Post’s systems were developed for the purpose of formalizing rules of inference in logic, and were very elaborate, allowing for conclusions to be derived from arbitrarysized finite sets of premises of arbitrary complexity. As soon as the concept of recursively enumerable (r.e.) sets was clearly formulated in the 1930s, it was clear to Post that any r.e. set of strings could be generated by one of his ‘canonical production systems’. In 1943 he proved that this remained true for dramatically restricted systems that he called ‘normal’ systems, in which every rule had the form ‘yX ⇒ Xz’ for specified strings y and z, where X is a free stringvalued variable, and in 1947 he proved the same for another special case, where the rules all have the form ‘X_{1}yX_{2} ⇒ X_{1}zX_{2}’, for specified strings y and z and variables X_{1} and X_{2}. This, of course, is exactly the form of the grammars that Chomsky (1959) later called ‘type 0’.
For any form of grammar that has this kind of expressive power (i.e., that can generate any arbitrary r.e. set), questions of the form ‘Does grammar G generate any string containing the substring w?’ are always going to be undecidable. This follows from Rice’s theorem (Hopcroft and Ullman 1979, 185–192) as applied to generative grammars rather than Turing machines. All nontrivial properties of r.e. sets (that is, properties that hold of some r.e. sets but not all) are undecidable.
I suspect it will also hold for the restricted class called contextsensitive languages (equivalent to the class of type 0 grammars in which the z is always at least as long as the y), though the conjecture needs a proof. The rationale for my conjecture is that nearly all decision problems asking for a property of an arbitrary contextsensitive stringset L are undecidable, the two exceptions being membership (‘Is w in L?’), which is decidable, and complement type (‘Is L contextsensitive?’), which was proved in 1987, surprisingly, to be trivial in the sense of having a positive answer for every contextsensitive L (this follows from the Immerman–Szelpcsényi theorem; see Immerman 1999, 149–151). Despite the decidability of membership, contextsensitive languages are extremely similar to arbitrary c.e. sets, and have essentially all of their complexity. Any type 0 grammar G over a symbol inventory Σ can be converted into a contextsensitive grammar G′ over Σ ∪ b where b is a new dummy symbol used for padding the ends of rules in which the right hand side is shorter than the left hand side. L(G) is then obtainable from L(G′) simply by ignoring b (where ‘ignoring b’ means applying a homomorphism that erases b).
The most interesting family of stringsets for purposes of studying the properties of human languages is the much smaller subset known as the contextfree stringsets (standardly called CFLs). This deserves closer attention. CFLs are generated by contextfree grammars (CFGs). It is by no means implausible that the set of grammatical sentences of English could be exactly generated by a CFG: see Pullum and Gazdar (1982), Pullum (1985), and Pullum and Rawlins (2007) for discussion of some failed counterarguments.
CFGs are far more tractable than contextsensitive grammars in most respects. But even for a CFG, it is not always immediately obvious what it can do. As a very simple example, consider the CFG with terminals {a,b}, nonterminals {S,A,B}, start symbol S, and the rules shown in [10].
[10]  S → aB  A → bAA  
S → bA  B → b  
A → a  B → bS  
A → aS  B → aBB 
The strings that this grammar generates are jumbles of a’s and b’s in arbitrary orders, but they all meet a special condition: the number of a’s is exactly the same as the number of b’s. The grammar in [10] generates all and only the strings meeting that condition. This could hardly be said to be immediately evident from looking at the rules, but it can be proved inductively (see Hopcroft and Ullman 1979, 81–82).
It follows that the grammar definitely allows for the construction of a sentence with aaa in it, and that any such string will also contain at least 3 instances of b, and so on. Indeed, we know for any arbitrary string of a’s and b’s that the answer to whether [10] can generate it is yes. However, that is specific to [10], and depends on the proof concerning what stringset it generates. Can we decide such questions more generally?
After all, although membership (‘Can the string w be generated by the CFG G?’) is decidable, and so is emptiness (‘Are any strings at all generated by the CFG G?’), many other semantic questions about CFGs (i.e., questions not about their form but about their meaning, in the sense of what strings they can generate under their usual interpretation) are formally undecidable. These include intersection emptiness (‘Does CFL L_{1} have a nonempty intersection with CFL L_{2}?’), stringset inclusion (‘Are all the sentences of CFL L_{1} included among the sentences of CFL L_{2}?’), regularity (‘Is CFL L accepted by a finitestate automaton?’), (see Hopcroft and Ullman 1979, 281), and many others.
The set of all strings of English words (whether grammatical or not) in which the substring of of of appears is clearly regular (finitestate), assuming only that English has a finite vocabulary V of words.^{1} The finite automaton accepting the set remains always in its start state q_{0}, checking only that each word is in V , and always rejects, except that if it encounters an of it switches to q_{1}, and if another one immediately follows that it goes into q_{2}, and if another immediately follows that it goes into q_{3}. Once in q_{3} it always accepts provided only that all subsequent words are in V . We seek a general algorithm for finding out whether some specific CFL has a nonnull intersection with that regular set. But the general question of whether two stringsets have a nonnull intersection is undecidable.
That is not in contradiction with what was said above about the rules in [10] and the set of strings containing aaa. There we had a specific CFG for which it happened to be possible to construct a proof that all the generated strings had equinumerous as and bs, and that some generated strings contained aaa. This shows that in certain special cases we may find out the answer. That does not give us a general algorithm for all cases.
I will return later to the question of whether, given a complete generative grammar for English, there would be a systematic general way of using it to guarantee answers to questions like [5]. But first I want to note an interesting similarity to a question in mathematics.
Question [5] has a particular logical property in common with the question in [11], which derives from a famous conjecture in number theory.
[11]  Is there an even number that is not equal to the sum of two primes? 
This can be easily stated using firstorder logic interpreted in the usual numbertheory model where the domain is the nonnegative integers with the operations ‘+’ (addition) and ‘⋅’ (multiplication). The predicate ‘even’ can be defined as in [12a]; ‘prime’ can be defined as in [12b]; and then [11] is the question of whether [12c] is true in the specified model.
[12]  a.  even(x) = _{df}(∃y[y ≥ 1 ∧ y ⋅ 2 = x]) 
b.  prime(x) = _{df}(¬(∃y∃z[y ≥ 2 ∧ z ≥ 2 ∧ y ⋅ z = x])) 

c.  ∃x[even(x) ∧¬(∃y∃z[prime(y) ∧ prime(z) ∧ y + z = x])] 
What [11] is in effect asking for is a counterexample to the strong Goldbach conjecture, henceforth GC, which claims that every even number greater than 2 is the sum of a pair of primes. Most number theorists are inclined to think this conjecture is true. One reason is that as we consider larger and larger even integers n, the number of different pairs of primes that sum to n increases, so that for any large n it is overwhelmingly likely that there is at least one pair that sums to n. But GC is a nonprobabilistic claim, and as is well known, no proof of it has been found, so currently it cannot be guaranteed that the answer to [11] is negative.
The logically interesting property that [5] and [11] share is that for each of them, showing that the question is algorithmically undecidable would ipso facto (though indirectly) tell us the answer. This sounds paradoxical, but it is not. It is a fairly simple point, fairly well known among number theorists and mathematical logicians.
Consider [11] first. To say that the answer to [11] cannot be discovered by an algorithm would mean that GC is unprovable within our system for proving things in arithmetic. And we know from Gödel (1931), of course, that some truths of arithmetic are unprovable in any system capable of expressing all arithmetical truths.
For concreteness, assume the standard system defined by the Peano axioms, known as PA, and a monadic secondorder logic interpreted on ⟨ℕ, +,⋅⟩ (the natural numbers with addition and multiplication). To say that GC is incapable of proof within PA is in effect to say that GC is independent of PA, in the sense that we could add GC to the set of PA’s consequences, or add its negation, without losing consistency either way. You could believe all the truths of PA plus GC, or believe all the truths of PA plus the negation of GC, and no one would be able to use PA to prove you wrong either way.
Yet if GC were shown to be independent of PA, we would immediately know whether it was true or not: it would have to be true, so the answer to [11] would be negative. Here is the reasoning.
If GC were false, there would be a counterexample, an even number that cannot be expressed as the sum of any two primes. Let g be that number. We could demonstrate GC’s falsity in an elementary way by simply exhibiting the list of all triples ⟨p_{1},p_{2},k⟩ such that p_{1} and p_{2} are primes and k ≤ g and p_{1} + p_{2} = k. The list might be very long, if g were very large, but it would be finite, and could be constructed by a very straightforward computer program. The absence from the list of any case where k = g would falsify GC, and thus answer [11] in the affirmative.
If [11] cannot be answered in the affirmative by a proof, the answer to it must be negative, i.e. GC must be true. The answer to [11] cannot be positive yet unprovably so.
An analogous result holds for [5]. If we found some way, using facts about a generative grammar for English, to show that [5] cannot be answered within some system of mathematical reasoning, then we would immediately (but indirectly) know that the answer to [5] is negative, because otherwise there would exist a sentence containing three consecutive occurrences of a single transitive preposition, and simply exhibiting the derivation of that sentence would settle the question, offering a proof of the positive answer. The answer to [5] cannot be positive yet unprovably so.
A key difference between question [5] and question [11] is that [5] is in a sense empirical. It is an empirical fact that those who describe themselves as speakers of English invariably regard All cows eat grass as grammatical but *Grass eat cows all as ungrammatical; they regard Never have I heard such nonsense as grammatical but *Never I have heard such nonsense as ungrammatical; and so on. If there is a sentence containing three instances of some transitive preposition in a row that English speakers treat as grammatical when it is presented to them, then that is an empirical fact (subject to all the usual epistemological caveats, to be discussed very shortly).
My guess, on the basis of 40 years’ experience of working on English syntax and techniques for formalizing syntactic theories, and six years working with Rodney Huddleston on the largest and most complete reference grammar currently available for English (Huddleston and Pullum 2002), would have been that the answer to [5] was negative: I would have thought that the rules of English grammar could not allow three consecutive occurrences of a strictly transitive preposition, on the grounds that there wouldn’t appear to be any context in which all three of them could have the obligatory nounphrase complements they require.
But it is a very important fact about argument and evidence in syntax that the intuition of a grammarian regarding generalizations of this sort cannot be trusted.
It is true that the intuition of a native speaker (whether a grammarian or not) can generally be trusted on individual sentences. This is why determining grammatical wellformedness for a sentence of reasonable length normally involves little more than having a native speaker look at it or listen to it, provided some minimal conditions of attentiveness are respected. But caveats are necessary even to that claim, because aspects of meaning, style, phonology, or processing may interfere with intuitive judgments about sentencehood. For example, [13a] will generally be judged grammatical, but the synonymous [13b] will not.
[13]  a.  Everybody whom everybody left departed. 
b.  Everybody everybody left left. 
This apparently because centerembedding a phrase or clause inside another, even once increases the processing load substantially. (Notice that the relative clause everybody left is embedded with parts of the main clause either side of it, which means processing of the main clause must be interrupted by the processing of another clause and then resumed where it left off; this is discussed in Miller and Chomsky 1963 and much subsequent psycholinguistic literature.) The combination of that with two pairs of adjacent duplicate words is confusing enough to completely wreck the chances of recognizing the grammatical structure.
Likewise, it is well known that there are sentences that confuse us into thinking they are ungrammatical by (as it were) tempting us to process them incorrectly. They are known as gardenpath sentences (Bever 1970). One celebrated example, well known from the psycholinguistic literature, is [14]:
[14]  The horse raced past the barn fell. 
Our tendency to process this with raced as the preteritetense verb of the main clause, and an unneeded extra verb fell on the end, is almost irresistible, and blinds us to the fact that raced can also be a past participle, so raced past the barn could be a nonfinite passive clause modifying horse. In other words, the sentence can be read with the same structure as [15]:
[15]  The car driven past the barn crashed. 
Many other similar examples could be given of the ways in which poor acceptability may wrongly make a properlyformed sentence seem ungrammatical.
However, even if native speakers can in typical cases intuitively perceive the wellformed structure of an individual sentence, even skilled syntacticians cannot reliably intuit the truth of generalizations about wide ranges of sentences or phrases.
The young Noam Chomsky ventured in a conference discussion the assertion that “The verb perform cannot be used with massword objects: one can perform a task, but one cannot perform labor” (Hill 1962, 29). Challenged by another participant (Anna Granville Hatcher) to say how he knew this, he answered: “Because I am a native speaker of the English Language.” Later in the discussion Hatcher asked him what he would say if the noncount noun were magic, and Chomsky was immediately forced to confess: “I think I would have to say that my generalization was wrong” (Hill 1962, 31).
On the specific point of whether a short sentence like They can perform magic is grammatical, or whether a short string of words like *They can perform justice is ungrammatical, he could supply reliable intuition reports, like most native speakers; but confirming a broader generalization about English sentence structure is a very different matter.
And to return to the case at hand, judging whether three consecutive transitive prepositions is possible in English is a judgment concerning an indefinitely large range of sentences. I would have hazarded the guess that the answer was negative, but I would have been wrong. The answer to question [5] is now known, thanks to Wells Hansen (personal communication), and it is positive. Hansen showed this by constructing and exhibiting, rather surprisingly, a grammatical sentence with an at at at sequence. A similar one is given in [16].
[16]  Donald Trump was laughed at at at least three dinner parties in Manhattan this year. 
It is fully grammatical (as well as probably also true), and surprisingly simple to understand. Of course, it might be impugned for style: a writer who notices that some word has been used three times within a short space, or that a jingle effect has been created by two or three words with a similar sound will generally reword. But that is about stylistic acceptability, not grammaticality.
Retrospectively, we can see why and how the Hansen sentence has to be regarded as grammatical. At occurs as a grammaticized preposition syntactically required in the construction laugh at:
[17]  a.  They laughed at him. 
b.  *They laughed to him. 

c.  *They laughed by him. 

d.  *They laughed on him. 
And the choice of preposition is determined by the choice of verb; other verbs require different prepositions:
[18]  a.  *We spoke at him. [speak does not take at] 
b.  We spoke to him. [speak does take to] 

c.  *We spoke on him. [speak does not take on] 

[19]  a.  *They rely at him [rely does not take at] 
b.  *They rely to him. [rely does not take to] 

c.  They rely on him. [rely does take on] 
Verbpreposition combinations of this sort readily yield prepositional passives (was laughed at, was spoken to, was relied on, etc.). Hansen’s sentence has the form of a prepositional passive clause, with the first at of the sequence as its stranded preposition. The subject of the clause (Donald Trump) is understood as the complement of the first at.
But at is somewhat more syntactically versatile than of in one respect: it can also serve as the head of a locative modifier like at three parties, which can occur following a prepositional passive; and it occurs in the idiomatic Preposition + Adjective combination at least, which can serve as an adjunct modifying a determinative like three, hence, crucially, can stand at the beginning of a noun phrase, as in at least three parties, and thus can begin a noun phrase serving as the complement of the preposition at.
Thus when the first at is stranded in a prepositional passive construction it is possible for a second atphrase heading a locative adjunct to follow, and for a third atphrase to begin the noun phrase within that locative adjunct. All those facts are relevant to why it is that at at at can be a possible subsequence in a grammatical sentence.
We should never forget that English syntax constitutes a vast domain of exploration, within which are many known unknowns, and an unknown number of unknown unknowns. This domain cannot be explored via the simplistic appeals to “logic” that purists and usage advisers so often advocate. Which sentences are grammatical is not determined by any kind of commonsense or formal logic. The grammatical sentences are simply the ones that happen to be permissible under the set of rules or constraints that defines the language — the large set of exceptionridden and often rather quirky rules that define English as it happens to be today. Discovering how we are to precisely formulate the content of those rules is a major scientific enterprise. Even an informal survey of the ground that must be covered takes up more than 1,700 pages of text (Huddleston and Pullum 2002, henceforth CGEL).
And we cannot blithely assume, even when we have produced such a grammar, that there will exist an algorithm for finding out whether it is possible for a grammatical sentence to meet some given condition, such as having three consecutive transitive prepositions, or containing the sequence and the of, or any other syntactically definable property of symbol strings. Indefinitely many precisely framed questions about human languages (considered as stringsets over a word vocabulary) are undecidable, even given a full, exact, and correct grammar for the language (which even for English, of course, we do not have as yet).
While in general native speakers (whether grammarians or not) have intuitive reactions concerning the grammaticality of specific strings of words presented to them, they do not have intuitional access to the truth values of generalizations about the entire range of sentences that are grammatical in their language, any more than mathematicians have intuitional access to the truth values of generalizations about the integers. The key difference is that we take the truths of number theory to be a priori and necessary, substantiable through rigorous proof as in the other formal sciences, while the true statements about English grammar are at root empirical.
We have qualified intuitional access to the status of specific sentences because we subconsciously respond to them as if we were encountering them in actual use, and to some extent we can report on our responses (see Devitt 1986, Chapter 7, for a discussion of this topic that I find very perceptive). But we have no veridical intuitional access to broader generalizations about the grammar of our language, and can be surprised by discovering them.
Questions about whether some word sequence like at at at or of of of can form a subsequence of a grammatical sentence in some human language, if we assume for concreteness that human languages can be generated by CFGs, have the general form seen in [20]:
[20]  Proper substring possibility 
Given a CFG G with terminal vocabulary V and an arbitrary string w in V ^{*}, does G generate any string that has w as a proper substring? 
One might ask whether there could ever be practical reasons for needing answers to such questions. Practical importance is of course something that in general we discover only retrospectively, but it is not impossible to imagine a context in which information about occurrence of substrings might be of practical use to an engineer. A robot equipped to parse and understand spoken English might be designed with a special simple word sequence that would immobilize it to permit servicing (or to block a Westworldstyle disaster in which robots become malign). To make sure the robot could not be immobilized unintentionally through ordinary conversation, one might want the word sequence to be one that definitely could not form part of any sentence of the language. We know, thanks to Wells Hansen’s discovery, that at at at could not serve that purpose. Maybe of of of could.
So is [20] formally decidable? The answer turns out to be yes. A problem closely related to it was studied by Lang (1988) in the context of devising a contextfree parsing algorithm that will yield useful output even when faced with sentences containing unknown parts of unknown length, by producing a finite representation of the set of all possible parses (perhaps infinitely many) that could allow for the missing parts. Subsequently Osorio and Navarro (2001) tackled more directly the problem of solving proper substring possibility as stated in [20], using the CKY algorithm as the basis for their proof and showing that the problem can be decided in cubic time.
Osorio and Navarro point out that the problem actually has many more areas of potential application than you might think, since CFG parsing is so closely related to other computational tasks like matrix multiplication and is so widely applicable: it could be relevant to DNA analysis in bioinformatics, syntaxdriven development of language tools, and shape analysis in pattern recognition.
Given a CFG for English, therefore, we could use a fully general algorithm to find out (in cubic time) whether, for example, there is a grammatical string with of of of as a substring. (I think there probably is, but I leave the exercise of constructing one for the reader to pursue in idle moments.) Of course, the algorithm presupposes the completion of a CFG that fully and accurately generates all and only the sentences of English. The informal account in CGEL, mentioned above, is not expressed in anything like the form of a CFG.
For what it is worth, Pullum and Rogers (2008) provide, in a rather unexpected way, good reason to believe that there is nothing in CGEL that is beyond the power of CFGs. They note that although the objects that CGEL uses as structural representations are not trees, they are very close to being trees, and the very limited departure from treehood that is employed (downward convergence of branches in certain particular kinds of noun phrase) can be described by a transduction to covering trees expressible in weak monadic secondorder logic (wMSO), and wMSOdescribable sets of trees always have CFLs as their frontier sets (by the theorem of Doner 1970). Hence CGEL appears to covertly entail that English (considered as a stringset over a vocabulary of dictionary words) is a CFL.
In principle, then, there almost certainly exists a CFG for English on which we could run an algorithm of the sort sketched by Osorio and Navarro to find out whether of of of (or any other word sequence) can be a substring of a sentence.
My thanks to Wells Hansen, whose serendipitous observation of an at at at sentence inspired this paper; to Colin Stirling, who discovered that the substring admissibility problem had been shown to be decidable by Osorio and Navarro (2001); to Marcus Kracht (originally an anonymous referee), who suspected that this was true and drafted a different proof from Osorio and Navarro’s, later generalizing it to cover all multiple contextfree grammars (MCFGs); and to my old friend and research collaborator András Kornai, who has taught me so much (though it will never be enough) about mathematically informed work on human languages.
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