Adding prepositional phrases to ask questions

Question

I have this problem. If I want to practice asking questions to each word in a sentence, then I will have the same structure in each question, like in these:

I was waiting for my sister.

Who was waiting for their sister? Who was I waiting for? Whose sister was I waiting for?

So, if my initial sentence is "I bought a book about animals.", I can ask "What did you buy? Who bought the book?"

Can we ask "What did you buy a/the book about?" My concern is the sentence structure. Is it possible? And, yes, I know we can ask "What was the book about?", but I don't want to add/change verbs.

In sentences like "I heard a song about love. I read an article about lions." my question would be the same. So is it somehow related to transitive verbs?

Answer 1

What did you buy a book about?

A straw poll of thirteen native speaker English teachers confirms that this sentence is perfectly grammatical, and in the right context totally natural too.

It might be worth mentioning that you don't seem to be able to extract the entire preposition phrase here though. The following is not grammatical, it seems:

• *About what did you buy a book.

The general principle

We can freely postmodify nouns by adding a preposition phrase:

• a painting by Picasso
• a book of charms
• a paper on Leonardo da Vinci

In the phrases above, the prepositions all have noun phrase complements. So we have a noun phrase with a preposition phrase modifier. Inside the preposition phrase there is a smaller noun phrase.

Generally speaking, when these larger noun phrases function as the complement of a verb, we can extract the smaller noun phrases to make a question:

• Who did you buy a painting by?
• What did you buy a book of again?
• Who did you write a paper on?

However, if we front the whole preposition phrase, the results are usually dubious:

• *By who did you buy a painting?
• *Of what did you buy a book?

However, if the preposition phrase can be construed as a complement of the verb as opposed to a modifier of the noun, then we might achieve a respectable result. So, for example we can write on a subject. So the following is acceptable:

• On whom did you write a paper?

Answer 2

The best I can think of (but it isn't perfect) is "What kind?" (in the US; maybe "what sort" in the UK): What kind of book did you buy? What kind of class did you take? What kind of bread did you buy? What kind of car did he drive? What kind of clothes was he wearing?

Note that in conversation (versus practice), sometimes a more specific word works better. For instance, you could say "what kind of shoes did you buy?" But in a conversation you probably want to know "what size shoe did you buy?" or "what style of shoe did you buy?" or "what brand of shoe did you buy?" and would ask the more specific question.

As for your question about intransitive verbs, if you want to know how to ask for more information about the object of a verb, you are by definition asking about a sentence with a transitive verb, so it's related in that sense. But "what kind" can also be used with intransitive verbs: "what kind of person does that?"

Answer 3

In theory you could say "What is the book you bought about?" which still uses the same verb to describe what was performed (buy), but in a different tense. It just changed the subject of the question, while still querying the question using the same general verbal concept.