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This question is relatively simple. I don't understand why we never use passive form of to infinitive after the adjective unless the subject is "it".

For example:

He is difficult to please.

People consider the example above a correct sentence. But:

He is difficult to be pleased.

People, for example, my teacher, said it sounds wrong and told me not to write this type of sentence. Is it grammatically flawed, or is it just a stylistic choice?

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    The second example is not commonly idiomatic. I suppose in this instance the two examples mean the same thing. But I can think of cases where they would have different meanings. E.g. Let's say my friend has broken a toe. I might say He finds it difficult to drive. That would have a rather different meaning to He finds it difficult to be driven. – WS2 Oct 3 '15 at 23:48
  • What's wrong with "He is happy to be pleased"? – deadrat Oct 4 '15 at 0:06
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    @deadrat The answer to your question is that difficult determines our interpretation of the object of the infinitive, whereas happy determines the subject of the infinitive. Because there is no object of a monotransitive verb when passived the OP's example is bad. But your example is fine because the subject slot of to be pleased is determined by the subject of the main verb. Your sentence means "He was happy [for him to be pleased]". Compare that with "He is difficult [for X to please him", where you can fill out X as you wish. Then compare that with ... – Araucaria - Not here any more. Oct 4 '15 at 0:27
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    @deadrat ... * "He is difficult [for X to be pleased him]". There is no object slot there for him to felicitously fill. – Araucaria - Not here any more. Oct 4 '15 at 0:29
  • @Araucaria I interpreted the title "infinitive used after adjective" to mean more than "infinitive used after difficult." The OP writes "the adjective," and if he means "that adjective" (i.e., difficult) my comment is inapt. If he means any predicate adjective followed by an infinitive, then his teacher has warned him off too broad a category of sentences. Your explanation makes sense, but it relies on the idiomatic circumstance that you can be happy for oneself but not difficult to oneself. If I have made this more opaque for Opaque, I apologize – deadrat Oct 4 '15 at 1:00
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Adjectives which take infinitival phrases as complement fall into three camps.

  1. Some adjectives determine our interpretation of the subject of the infinitival clause.

  2. Some adjectives determine our interpretation of the object of the infinitival clause.

  3. Some adjectives don't determine our interpretation of either the subject or the object of the infinitival clause.


Group 1

Adjectives in the first group are often called control adjectives. Generative linguists would say they involve Equi deletion. For our purposes it isn't important what we call them. Let's look at an example:

  • Bob was keen to finish his book.

The adjective phrase headed by keen is the complement of the verb BE. Within the phrase, keen is taking an infinitival clause:

  • to finish his book

This infinitival clause has an understood subject. The subject must be the same as the subject of the main verb, BE. The sentence means:

  • Bob was keen [for Bob to finish his book]

So when we use the adjective keen like this, the subject of the main clause controls our interpretation of the subject of the infinitival clause. Some other adjectives like this are anxious, delighted, eager.

Notice that these adjectives only work this way if we don't overtly mention the subject of the infinitival clause. If we actually mention a different subject, the sentence will still be fine:

  • Bob is keen for Mary to finish her book.

The adjective keen only determines our interpretation of the subject if we don't state who the subject actually is.

Lastly notice that we can easily use passive infinitivals with adjectives like keen. Passive infinitivals still have an empty subject slot which can be filled:

  • Bob was keen to be kissed by Mary.
  • Bob was keen [for Bob to be kissed by Mary].

There's no problem using passive infinitival clauses with adjectives like keen


Group 2

Some linguists who talk about these adjectives, talk about adjectives which take hollow clauses. Others talk about adjectives that involve tough movement. Again, it doesn't matter what we call these adjectives here.

Let's look at an example:

  • The orangutans are difficult to please.

Again we see an adjective phrase functioning as the complement of the verb BE. Again this adjective is taking an infinitival clause as its own complement. This infinitival clause has a vaguely understood subject. The subject of the infinitival clause isn't determined by the grammar. The listener can just mentally fill in the subject with whoever they think is suitable. In the sentence above the subject of the verb please is just people in general. We can reconstruct it like this:

  • The orangutans were difficult [for people to please]

If we change the sentence we will get a different understanding of the subject:

  • I found the orangutans difficult to please.

This sentence probably means:

  • I found the orangutans difficult [for me to please].

It doesn't have to mean that though. It could mean that I found that zookeepers generally found the orangutans difficult to please. The subject of the clause is just determined by our interpretation of the context.

However! I haven't given the complete picture here. The verb please usually takes an object. But the object of the infinitives in the examples above is missing. I should have modelled our interpretation of the example above like this:

  • The orangutans are difficult [for people to please ___ ]

Here our interpretation of the object slot there is strictly determined. It's determined by the subject of the matrix verb, the subject of the main clause. So we understand the sentence like this:

  • The orangutans are difficult [for people to please them]

Here, our interpretation of the object of the infinitive is determined by the subject of the main verb.

Now notice that if we make the infinitival into a passive, the object slot will disappear. Passive clauses don't have an object slot, usually, because the object of the active version of the clause has been turned into the subject of the passive one. There is no object slot to fill. This means that if we use a verb like difficult with a passive infinitival in a sentence like this, the sentence will be badly formed:

  • *The orangutans were difficult to be pleased.

If a native speaker reads this sentence it will hurt their language brain. The speaker obviously wants the orangutans to fill the subject slot of be pleased. The grammar won't let this happen. Our brains are already trying to fill in some kind of object slot after the verb please with the orangutans. This results in a car crash:

  • *The orangutans were difficult [for someone to be pleased the orangutans]

Other adjectives like difficult are dangerous, strange, good, bad, impossible.


Group 3

Some adjectives don't fall into groups 1 or 2. We can't use them as predicate adjectives when they have an infinitival clause as complement. That is to say we can't use such adjective phrases as Predicative Complements. One of these adjectives is the word possible:

  • *A Rubik's cube is possible to be done.
  • *Pineapples are possible to grow here.
  • *Whales are possible to swim.

These sentences are ungrammatical. They are odd because they seem to be verging on the grammatical, but just don't seem to quite work properly.


Extrapositions using dummy it

We can use the adjectives from group three in sentences involving extrapositions. These sentences use the dummy pronoun it.

  • It is possible to do a rubix cube.
  • It is possible to grow pineapples here.
  • It is possible for whales to swim.

Notice that if we state the subject of the infinitival clause it must be preceded by the subordinator for, as in the whales example.

We can also use adjectives from group 2 in extrapositions. When they appear in extrapositions, our interpretation of the object isn't determined, it's understood from the context. I've taken these useful examples from WS2's comments

  • After my car accident it was difficult to drive.

Here we understand that I probably find it difficult to drive cars. Notice that because the interpretation of the object slot isn't grammatically determined, we can freely use passive infinitivals here:

  • After my car accident it was difficult to be driven.

Note that we don't seem to be able to use adjectives from group 1 in extrapositions:

  • It was keen to leave.

This only makes sense if we understand it as being an actual thing. It cannot be a dummy pronoun here.


Notes

1. Adjectives phrases like those in groups 1 and 2 normally function as predicative complements. Predicative complements can describe either the subject or the object of the verb. I have oversimplified things in the story in the post above. I have said that the subject of the matrix verb determines our interpretation of the subject or object of the infinitival, but what determines this is actually the predicand of the predicative complement, not necessarily the subject. So in Bob was eager to please the adjective phrase eager ... describes Bob and therefore Bob is interpreted as the subject of please. But in Bob found Mary eager to please the adjective phrase eager ... describes Mary and so Mary is understood as the subject of the verb please.

2. Yes, possible and impossible are in different groups. Crazy, isn't it.

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    @Opaque Because tough adjectives like difficult must have an empty object slot in the infinitival clause. If there isn't one the sentence won't work. Notice though that you could make a version of your desired sentence though: "Orangutans are difficult for orangutans to please". This is because there is still an empty object slot in the infinitival clause. It means "Orangutans are difficult for orangutans to please [them]". In this sentence we understand the object of "please" to be the subject of are = i.e. the orangutans! – Araucaria - Not here any more. Oct 4 '15 at 2:17
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    "Pineapples are impossible to grow here" is perfectly okay. – Greg Lee Oct 4 '15 at 2:26
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    @Araucaria, "possible to grow" is pretty good -- I'm still mulling it over. – Greg Lee Oct 4 '15 at 2:32
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    And if it does, why can't I use extrapositions with dummy subject "it" with adjectives from first group? Saying "it was sad to watch my tem lose" is correct, isn't it? – Opaque Oct 4 '15 at 2:47
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    @Araucaria It does seem a crazy state of affairs when one can say, perfectly grammatically The dinner is ready to eat, are you? – WS2 Oct 7 '15 at 15:15
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*"He is difficult to be pleased" is ungrammatical. The object of the infinitival verb can be made subject ("He is difficult to please [him]"), but the subject cannot ("He is difficult to [him] be pleased").

Why does it work that way? I don't know. The syntactic rule involved is tough-movement, which has a Wikipedia entry, Tough movement.

  • I do not understand how "he is diffichlt to please him" makes sense...I'm not a native speaker, so can you explain? I thought that I should not put "him" after the to infinitive associated with though movement... – Opaque Oct 4 '15 at 1:12
  • "He is difficult to please him" does not make sense. I'm sorry that I gave a confusing shorthand of indicating that the "he" subject is derived from the original object of "please". Did you look up my reference? It is pretty clear. – Greg Lee Oct 4 '15 at 1:28
  • I did. Thank you for the reference. But when the passive to infinitive is used with adjective, it seems to me that only adjectives associated with someone's feelings, such as happy, sad, etc. can be followed by those passive to infinitives (ex: happy to be a teacher). Why is that so? – Opaque Oct 4 '15 at 1:33
  • I don't understand your question. Your example "happy to be a teacher" does not have a passive "to" infinitive. Adjectives and verbs associated with feelings have some special syntactic properties -- they are called "emotives". – Greg Lee Oct 4 '15 at 2:22
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    @Araucaria, not me. I never downvote anything, much less you. – Greg Lee Oct 4 '15 at 2:30
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Short Answer

He was difficult to please ___ .

In the sentence above, we do not state what the object of the verb please is. Our interpretation of the object of this infinitive is determined by the subject of the main verb, he. We understand the sentence as :

  • He is difficult [for someone to please him]

This is because the infinitival clause is the complement of the adjective difficult. Other adjectives don't necessarily work the same way. [Adjectives like difficult are said to take "hollow clauses", generative linguists call them "tough adjectives"]

If we passivise the infinitival clause, the sentence will be badly formed because there is no longer any object slot after the verb please. We will have trouble parsing the sentence properly:

  • *He is difficult [to be pleased him] (ungrammatical)
  • Any reason for the down vote? – Araucaria - Not here any more. Oct 4 '15 at 2:20
  • I don't see any... – Opaque Oct 4 '15 at 2:24
  • @Araucaria Yep, another DBDV, a plague on this site. Let me fix that for you. – deadrat Oct 4 '15 at 2:45
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    Now that I understand it, it was pretty simple concept.. Thank you for the effort you put in to help me, Araucaria! – Opaque Oct 4 '15 at 3:54

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