Syntax I

So, perhaps you’re trying out the Topicalization tests, and you may well be finding that the judgments are a bit harder to make than anticipated. Let me give you a couple of notes about judgments, if this helps.

Our theory is such that at this point we only have a way to distinguish “grammatical” from “ungrammatical”, but yet our intuitions on the “goodness” of a sentence are significantly more squishy than that. One problem is that there is kind of an unavoidable tendency to give a sentence the benefit of the doubt, grammatical until proven otherwise. It’s clear what the sentence means, so it is sometimes possible to overlook that it might not be a great sentence. Still, if you can only imagine it being said by Yoda, that doesn’t really qualify it as a good English sentence.

It’s also worth being aware that wh-islands are perhaps extra-squishy, and it’s relatively easy to find examples of a wh-island violation that sound pretty good. So, for example, (1) and (2) don’t really sound too bad, although they are wh-island violations.

(1) ?Which movie did you forget whether you returned to Blockbuster?
(2) ?What did you wonder who stole? 

On the other hand, (3) sounds gut-wrenchingly horrible.

Scenario: John stole a bunch of things. Your friend remembers almost all of the details, what he stole, how he stole them, but she says that there’s one method that he used that she’s now forgotten how he used it — that is, what he stole using that method. You wish to inquire what the method was.

(3) *How did you forget what John stole?

Given that, a good strategy might be to first consider how bad the wh-question version of your topicalization test sentence is. If you find that the wh-island violation doesn’t sound too bad in a wh-question, then it’s not going to be very surprising to find that the topicalization doesn’t sound too bad either, regardless of whether topicalization is constrained by islands or not. So, you want to try topicalization out on those sentences for which wh-questions sound worst when the wh-phrase comes out of an island.

This is true with most of the islands, some are worse than others. Also, don’t forget that when you are checking complex noun phrase islands, the complex noun phrase needs to be definite. So, with either the or my or something (3-5)—indefinite DPs don’t seem to act as islands (6-7).

(4) *What did John read the book about?
(5) *What did John read my book about?
(6)  What did John read a book about?
(7)  What did John read books about?

You might also try making the sentences a bit more complicated, that can exacerbate any slight ungrammaticality. So, (8) and (9) are both adjunct island violations with basically the same structure, but (9) sounds worse. Well, somewhat, anyway.

(8) ??What did John laugh before he told Mary?
(9) ?*What did John rapidly start feeling nauseous before he told his best friend?

What the exercise is really about is coming up with sentences that would tell you whether topicalization seems to be constrained by the same islands that wh-movement is constrained by. Your final conclusion is not that important, except insofar as it follows from the judgments you report, although—as with wh-movement—there’s kind of a canonically accepted answer out in the field.