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You gave him the book. (1)

Based on the sentence (1), it seems to me that the following form of question is possible:

Whom did you give the book? (2)

instead of

To whom did you give the book? (3)

since him is an object of the verb "give".

I know (2) is rare. But, is (2) ungrammatical?

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Consider "Whom did you send to the inquisitors?" and "To whom did you send the inquisitors?" If you drop the tos, how are you going to figure out what "Whom did you send the inquisitors?" means? – Peter Shor Feb 2 at 14:56
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@Peter: Another incisive example, as with your Suspect: "Try and convict me." Prosecutor: "Have it your way. We'll try and convict you." – FumbleFingers Feb 2 at 15:07
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One thing you state in your question is not exactly correct. "Him" is the indirect object of the sentence; "book" is the direct object. See this explanation: dailygrammar.com/Lesson-191-Indirect-Objects.htm – JLG Feb 2 at 15:16
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Nowadays nearly everyone will say: "Who did you give the book to?" The "To whom....?" construction is normally reserved for formal writing, and it's practically becoming obsolete or archaic. In twenty years time, it will have disappeared from the spoken vernacular. – Mari-Lou A Feb 2 at 15:17
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@PeterShor: That's like saying "I sent him a letter" is ambiguous because then how can we figure out what "I sent him" means. – sumelic Feb 3 at 0:10
up vote 8 down vote accepted

Saying "Whom did you give the book?" is rare seems to me an understatement; I haven't found any actual examples of sentences like this. (As far as I know, who can always be used instead of whom, so I'm treating "Who did you give the book" the same way in this answer.) Despite the rarity, I have found conflicting statements from grammar experts about whether it is definitely ungrammatical (which may reflect a similar variance in native speakers' intuitions.) All of them agree that is is at the very least infelicitous for many speakers.

As ChongDogMillionare said, the fact that we can say

You gave him the book.

(using a noun phrase "him") as well as

You gave the book to him

(using a prepositional phrase "to him") is called dative alternation. We can use the noun phrase form in some complex sentences, such as passives (He was given the book) and interrogative sentences where the direct object is fronted (What did you give him?).

So, your question is basically: can we use the noun phrase variant in an interrogative sentence with a fronted indirect object? (Whom did you give the book?)

My intuition is that you can't. But I don't know why not! In the comments, Ben Voight gave an example sentence You gave whom the book? and suggested it was grammatical. I don't know if I agree; it sounds awkward to me, but I don't know if that means it's ungrammatical. If it is grammatical, and Whom did you give the book? isn't, then the issue must be with the fronting specifically. There are other syntactic differences between questions with fronting/wh-movement and those with wh-in-situ, like the use of an auxiliary (did in this case).

Here is a relevant quotation that says the sentence is ungrammatical for this reason:

Wh-movement distinguishes between direct and indirect object: *Who did you give a book?; What did you give John?

(Essays on Anaphora, by H. Lasnik)

It's a convention in linguistics to use a preceding asterisk to mark a sentence as ungrammatical. But I also found this:

Wh-movement of the indirect object from the V NP NP frame is generally regarded as infelicitous. Fodor (1978) explains this with reference to a processing restriction she terms the XX Extraction Constraint. In parsing a string in which the indirect object has Wh-moved, the parser would have difficulty detecting the gap since its expectation that an NP will follow the verb is in fact met by the direct object NP. [...]

?Who will the children show the new toy?

("Prior Linguistic Knowledge and the Conservatism of the Learning Procedure: Grammaticality Judgements of Unilingual and Multilingual Speakers", by Helmut Zobl)

The wording here doesn't seem quite as strong ("infelicitous") and a question mark is used, which indicates less certainty that it is ungrammatical than an asterisk would.

And here is another quotation that implies that some speakers find it grammatical, even though many others don't:

Testing superiority effects in English double object constructions is also tricky, since for many speakers wh-movement of indirect objects is impossible even if the indirect object is the only wh-element. However, for speakers that do allow wh-extraction of indirect objects, the predicted contrast does appear to hold, as shown in (85a-b).

(85) a. ?? Whomi did John give ti what?
b.* Whati did John give whom ti?

(Symmetry in Syntax: Merge, Move, and Labels, by Barbara Citko)

Here, ti represents an imperceptible trace left behind before the indirect or direct object is moved.

I found a source that points to some further discussion:

Another asymmetry[...] has often been noticed in the literature on double object constructions (cf. Hudson, 1992; Larson, 1988; Oehrle, 1976):

(11) a. What did she send her sister t?
b. ?*Who did she send t a book?
c. Her sister was sent t a book.
d. ?*A book was sent her sister t.

[...]Wh-Movement can extract the direct object in a double object construction, whereas NP movement can extract the indirect object. Neither of these processes is problematic. However, the reverse pattern of extractions is problematic for many speakers (cf. Hudson, 1992, who discusses variability in judgements here.)

("Constraints on Argument Structure," by Kenneth Hale, Samuel J. Keyser, in Syntactic Theory and First Language Acquisition: Cross-linguistic perspectives Vol. 1 Heads, Projections, and Learnability by Barbara Lust, Margarita Suñer, John Whitman)

I found a PDF of the relevant paper by Hudson, "So-called “double objects” and grammatical relations."

I also found an interesting example sentence that seems similar but is treated as grammatical, although it has an additional interrogative word:

Who did you give what at Christmas?

(Pragmatic Syntax, by Jieun Kiaer)

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Thank you for the detailed explanations and enlightening comments. I've found some books you mentioned. So, I will spend some time reading them. – Aki Feb 3 at 7:50
    
One possible reasoning I found is that the indirect object is not questioned since only the last part (direct object) carries a new information. What do you think? – Aki Feb 3 at 8:11
    
@Aki: I still have to finish reading Hudson and think about what he says. The idea that it has to do with information structure is interesting; I wonder if that is why two of the examples sentences where it is treated as being possibly grammatical have a second question word as the direct object ("Whom did John give what?" and "Who did you give what at Christmas?") – sumelic Feb 3 at 8:23
    
> two of the examples sentences where it is treated as being possibly grammatical have a second question word as the direct object. Yes, of course! – Aki Feb 3 at 10:11

Yes, (2) is ungrammatical.

You gave him the book is You gave the book to him after it goes through Dative alternation. After flipping the direct object and indirect object, the to preposition disappears.

You can't do this with questions, so you need the to.

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The interrogative pronoun who can't be used as an indirect object or dative case (in other words). It is only used as a subject or in place of whom. There is no dative alternation between who and whom. Whom can't be used in place of who. Your answer is misleading. – Rathony Feb 2 at 15:50
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@Rathony What? where in my answer does it state that? Your comment is misleading – ChongDogMillionaire Feb 2 at 15:54
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How can you explain "Who did you give the book to?" Is it ungrammatical? – Rathony Feb 2 at 16:09
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@ChongDogMillionaire: Your clear claim is wrong. Both "You gave whom the book?" and "You gave the book to whom?" are perfectly grammatical, as are "You gave him the book?" and "You gave the book to him?". The rule you are trying to express, if any exists, has something to do with word order and nothing to do with questions. – Ben Voigt Feb 2 at 17:22
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@BenVoigt In your second question, dative alternation doesn't take place. Your third question is just a declarative statement with a different inflection at the end indicating it's a question. Your first question is interesting, you're just replacing him/her with whom... not sure if that's a formal or grammatical way of writing a question. I would agree all are idiomatic in speech though. – ChongDogMillionaire Feb 2 at 17:30

1)/You gave the book to him/ is the declarative form of:

To whom did you give the book? A standard English formal form

2)/You gave him the book/ is the declarative form of:

Did you give him the book

That said, in colloquial spoken English, nowadays, people will often say:

Who did you give the book to? for 1)

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Don't forget that "you can never end a sentence with a preposition". ;) (disclaimer: I consider that rule outdated nonsense and will end sentences with prepositions if I want to) – John Clifford Feb 2 at 15:16
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I thought I had accounted for that rather specifically. Standard formal English plural versus colloquial spoken English. Isn't that eggs in your beer?? – Lambie Feb 2 at 15:19
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Hypothetically, what about Whom did you give the book to? – Stu W Feb 2 at 15:19
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/Whom did you give the book to/ is grammatical also, though not ""hyper formal". What isn't grammatical is: /Whom did you give the book/ – Lambie Feb 2 at 15:23
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The relationship between "You gave the book to him"/"To whom did you give the book" is not the same as the one between "You gave him the book"/"Did you give him the book?" The equivalent interrogative sentence for the first sentence would be "Did you give the book to him?" The original post asks if "Whom did you give the book?" is grammatical; can you please answer this explicitly in your post? – sumelic Feb 3 at 2:25

It's not technically correct. but most people would understand it, since in English, you can generally drop extra words as long as your meaning is still clear in context.

Let's consider another form: Whom did you give the book to? (4)

These sentences (2) What place did you go? (3) To what place did you go? (4) What place did you go to? are all equivalent to a native speaker, although (4) sounds a little wordy.

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'What place did you go?" seems to have the same problem as "Whom did you give the book?" Normally, I would use "to" at the end of both of these. (Well, actually, in this specific case I would use "Where did you go?") – sumelic Feb 3 at 0:01
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Even though I don't think I would drop "to" in this context, it seems plausible to me that some people would, but do you have any examples or prior discussion you can point to? – sumelic Feb 3 at 2:27

Unusual but almost correct ! Here's why ? "Whom did you give the book ?" is rather complex to let's think you could save the preposition to with whom. But "Whom did you read ?" works because it's a direct interrogative. "Whom are you talking to ?" also because we have a complete sentence. So you can't forget the to with an accusative ; if you do so, drop the accusative ! "Whom are you talking ?" is not correct either. And "Who did you give the book" seems to me acceptable beside we don't know exactly who gave the book to whom :) in a question where we may have an inversion of the verb... So that's why you wanted Whom to start !

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