Who does John think it is amusing that likes Jill?

[Phaedrus]

Greetings,

It is well received that if one wishes to make a wh-question focused on the underlined element in a sentence like

(a1) John said that Jack likes Jill.

one can do so whether one includes that or not

(a2) Who(m) did John say (that) Jack likes?

whereas if one wishes to make a wh-question focused on the subject of the same clause

(b1) John said that Jack likes Jill.

one cannot do so grammatically unless one deletes that:

(b2) Who did John say (*that) likes Jill?

My interest here is in the forming of wh-questions relating to subject and object in a different kind of embedded that-clause:

(c1) John finds it amusing that Jack likes Jill.
(d1) John thinks it is amusing that Jack likes Jill.

If you had to rate the following sentences, would you choose (1) grammatical, (2) borderline, or (3) ungrammatical?

(c2) Who(m) does John find it amusing that Jack likes?
(c3) Who does John find it amusing that likes Jill?

(d2) Who(m) does John think it is amusing that Jack likes?
(d3) Who does John think it is amusing that likes Jill?

If you find any of them borderline or ungrammatical, and I can't deny that I hope you do, would it make a difference if that were omitted? Can it be?

Thank you!

[jutfrank]

(c2)=1
(c3)=3 (omission of that makes no difference)

(d2)=1
(d3)=3 (omission makes no difference)

Please let me know what you conclude.

[Phaedrus]

(c2)=1
(c3)=3 (omission of that makes no difference)

(d2)=1
(d3)=3 (omission makes no difference)

Please let me know what you conclude.

Thanks, Jutfrank. I agree with your judgements.

There seems to be what syntacticians call an "island" effect in extraposed that-clauses, in so far as their subjects are concerned.

Initially, I had hoped that the examples with the objects questions were also bad, or at least borderline, since that would seem more logical.

However, the sentences in which the objects of the extraposed that-clauses are questioned seem undeniably OK.

I think the following example shows the effect in the simplest way possible:

Basic sentence: It is amusing that Jack likes Jill.
Object of extraposed that-clause questioned: Who(m) is it amusing that Jack likes?
Subject of extraposed that-clause questioned: *Who is it amusing that likes Jill?

Of course, without extraposition, even the object question won't work.

From That Jack likes Jill is amusing the following can't even remotely be made. These are beyond ungrammatical. They are insane.

*Who(m) that Jack likes is amusing?
*Who(m) does that Jack like is amusing?
*Who that likes Jill is amusing?

[tzfujimino]

Who that likes Jill is amusing?

Jack.

[Alexey86]

Subject of extraposed that-clause questioned: *Who is it amusing that likes Jill?

What about Who(m) is it amusing that Jill is liked by?

[Phaedrus]

What about Who(m) is it amusing that Jill is liked by?

Interesting question, Alexey. Elegance aside, we can certainly change Who likes Jill? to Who(m) is Jill liked by? or By whom is Jill liked?

That said, I get an ungrammatical vibe from ??Who(m) is it amusing that Jill is liked by? or ??By whom is it amusing that Jill is liked?

I wonder what Jutfrank, GoesStation, and any of my other fellow native speakers here who may be following this thread think.

Perhaps your sentence makes a good candidate for the category 2 ("borderline") designation. Tentatively, I'm giving it a 3.

[jutfrank]

What about Who(m) is it amusing that Jill is liked by?

I wonder what Jutfrank, GoesStation, and any of my other fellow native speakers here who may be following this thread think.

Hmm. I'll give it somewhere between a 2 and a 2.5

[emsr2d2]

What about Who(m) is it amusing that Jill is liked by?

I'll be brutally honest here - I hate that sentence! I genuinely wouldn't be able to work out what it was trying to express if I read it elsewhere.

[Alexey86]

I'll be brutally honest here - I hate that sentence!

I hope nobody got PTSD after reading my sentence.

[emsr2d2]

Post-Traumatic Sentence Disorder?