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This grammar question below was asked of a Japanese colleague of mine. Questions (1) and (2) do not sound at all natural to me as a native speaker, even in the most formal of situations; however, I cannot provide a grammatical explanation to support or refute my assertion. Could anyone shed some light on the questions posed below?

Thanks in advance,
Steve

> I have a favor to ask of you. I would like to know the grammatical status
> of the sentences (1)-(3). Are they acceptable (ok), marginal (?) or
> unacceptable (*)? Crucally, the status of (3).
>
> (status)
> (1) ( ) Which picture of who(m) did you like?
> A possible answer to this question may consist of multiple pairs of the
> photographer and the subject, for example (I guess).
> E.g., "I liked John's picture of Ann (not Edwin's picture of Susanne, etc.)
> and Ray's picture of Margaret (not Richard's picture of Sam, etc.)"
> (2) ( ) I wonder which picture of who(m) you liked.
> (3) Who do you wonder which picture of he liked?
>
> I am assuming that (1)-(2) are acceptable. Are they?
> My concern here is with the question whether it is in general possible to
> extract an interrogative word/phrase (e.g. "who(m)" in (3)) out of a larger
> interrogative phrase (e.g. "which picture of who(m)" in (3)), as in (3). It
> should not be possible, given "my theory" I am advocating in my paper (in
> preparation).
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Comments  
Hi Steve,

Welcome to the Forum.

This grammar question below was asked of a Japanese colleague of mine. Questions (1) and (2) do not sound at all natural to me as a native speaker, even in the most formal of situations; however, I cannot provide a grammatical explanation to support or refute my assertion. Could anyone shed some light on the questions posed below?

I have a favor to ask of you. I would like to know the grammatical status
of the sentences (1)-(3). Are they acceptable (ok), marginal (?) or
unacceptable (*)? Crucally, the status of (3).


These all sound very awkward, and in fact unacceptable, to me. It seems to me that you are asking two questions at once, and the second one needs to be more explicit.

(1) ( ) Which picture of who(m) did you like?


If you say 'which', you may get an answer like 'The one in front of the tree, with Tom sitting on the ground', so I'd say 'whose'.

Whose picture, and of whom, did you like?

A possible answer to this question may consist of multiple pairs of the
photographer and the subject, for example (I guess).
E.g., "I liked John's picture of Ann (not Edwin's picture of Susanne, etc.)
and Ray's picture of Margaret (not Richard's picture of Sam, etc.)"
(2) ( ) I wonder which picture of who(m) you liked.

I wonder whose picture, and of whom, you liked?

(3) Who do you wonder which picture of he liked? This is an extremely awkward thing to say. It's so hard to understand the meaning that it seems wrong.

Perhaps Whose picture, and of whom, do you wonder that he liked?

I am assuming that (1)-(2) are acceptable. Are they?
My concern here is with the question whether it is in general possible to
extract an interrogative word/phrase (e.g. "who(m)" in (3)) out of a larger
interrogative phrase (e.g. "which picture of who(m)" in (3)), as in (3). It
should not be possible, given "my theory" I am advocating in my paper (in
preparation).

Best wishes, Clive

Hi Steve,

Sorry to blow it so spectacularly on your first post, but I really strike out on this one. I hope another member comes along and rises to the occasion. I'm just a regular member, but welcome to the Fora.

The only things making any sense to me are your request for help and your sample answer, "I liked John's picture of Ann (not Edwin's picture of Susanne, etc.)" How in tarnation you were able to arrive at that from the question as posed is beyond me. I look forward with some trepidation to the release of your paper.

This is really a great site with some very talented staff and regulars.

Apologies again, - A.
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Thanks very much for the welcome.

Just to clarify: the message in quotes is not mine, but that of a Japanese colleague at my university. He is the one writing the paper.

None of the statements in 1-3 sound correct to me. However, my Japanese colleague is assuming that (1) and (2) are acceptable, to which I would reply that they do not sound grammatical to me. However, I cannot provide a grammatical explanation as to why they sound ungrammatical. I'm looking for a grammatical explanation.

Thanks,
Steve
Hi Steve,

My problem is, the constructions are so bizarre and unlikely I can't even guess what's intended. That would almost be a prerequisite to offering a recommentation.

I'll try again after I've had some rest. I'll see if I can "provide a grammatical explanation as to why they seem so ungrammatical."

Best wishes, - A.
Hi again, Steve,

OK, let me have another go at this. I'm just going to focus for the moment on #1.

(1) ( ) Which picture of who(m) did you like?

There are two separate questions here.

Which picture did you like?

Of whom did you like the picture?

Grammatically, one would combine these questions by using 'and', ie

Which picture did you like and of whom did you like the picture?

One could then eliminate the repetition, arriving at Which picture, and of whom, did you like?

I can see no grammatical justification for continuing by eliminating the 'and', as was done in the original.

What do you think about this approach?

( I'm intrigued by the idea that people in Japan are writing papers on such sentences. )

Clive
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I agree -- the questions all have to be divided into two parts.

Another problem with this very problematic sentence Which picture of who(m) did you like? is the ambiguity of "of whom". This remains even if you change it into the slightly more manageable "Which picture did you like? And of whom?" Does it refer to the person in the picture, or the person who took the picture?

If you say "Which picture of Ann did you like" it would mean choosing among the picture of Ann in a red dress, the picture of Ann by the sea, the picture of Ann as a baby, etc.

If you say "Which picture of Ann's did you like," it means choosing among several pictures taken by Ann -- Ann's picture of her dog, Ann's picture of her cat, Ann's picture of the Eiffel Tower, etc.

I don't know which of these questions the original sentence is trying to ask. (Which picture did you like? And was it a picture of Ann, or of Ted, or of Mr. Pedantic?") or (Which picture did you like? And was it by Matthew Brady, Diane Arbus, or Edward Steichen?)
Steve S.However, I cannot provide a grammatical explanation as to why they sound ungrammatical. I'm looking for a grammatical explanation.
In the grammatical terminology and usage I am familiar with, which and whom are either interrogative pronouns or relative pronouns. In the sentences they are neither and thus incorrect.

CB
Hi CB,

In ' Which picture . . . ?', which is an interrogative adjective.

Clive Emotion: smile
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