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Suppose a person has been accused of doing something wrong and a cunning policeman is questioning him. Suppose the police is asking questions in such a way that it is very likely that the accused person is likely to be found out if he, in fact, had done something wrong.

What can we say about the type of questions the policeman is asking. I am looking for an adjective like "trappy", if there were such a thing, meaning "full of traps". Are there any words like this?

EDIT- I would like to point out that please don't take my example as if the word could be used with Police procedure only. That was mere an example to let you understand the scenario. The word may describe conversation by anybody. Even one of my friends can also ask such questions of me if he/she has some doubts about me.

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You might also call these questions tricky or trick questions. The notion that they are trying to trap the suspect suggests the possibility of entrapment. Although the definition refers to tricking someone into committing a crime, I think it can be extended to tricking someone into incriminating himself by saying things that indicate guilt, including a false confession. However, I also like Jim's two suggestions plus trenchant. –  user21497 Jan 28 '13 at 7:50
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@BillFranke - I believe yours is a much better word. Why don't you put it as an answer? –  Mohit Jan 28 '13 at 9:09
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4 Answers

You could continue the trap metaphor with trap-laiden.

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Or trap-laden? Laden as a pa.p of 'to lade', meaning to load. I'm not sure 'laiden' exists as a pa.p. –  Mynamite Jan 28 '13 at 16:46
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I think pointed questions and loaded questions are two excellent candidates, put forth by Jim and coleopterist, respectively.

I'd like to add one more to the list: leading questions. From NOAD:

leading question (n.) a question that prompts or encourages the desired answer

Leading questions are sometimes considered to be an unfair interrogation technique. One website mentions:

Leading questions are those that nudge, push or shove the other person towards a particular answer and away from other answers. They are a very common form of bias.

Also, the difference between leading questions and loaded questions is discussed some on Wikipedia.

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Police interrogation techniques include the use of loaded and suggestive questions.

Unethical or unskilled police officers can use suggestive questioning in interrogation rooms. Such interrogators use different kinds of techniques and questions in order to get people to confess. They use response framing when getting people to falsely confess. This is when they purposely limit certain answers and suggest others. For example, they would ask someone if they were at the house at 1, 2, or 3 o’clock, forcing them to think it had to have been one of those choices. It causes people to recall things from the prompt instead of their memories. Also, interrogators use stereotype induction, which is when they tell the witness only negative characteristics of the alleged perpetrator. Part of stereotype induction is the incriminating condition where everything the witness says is labeled as bad. The detective would slightly shake his head or tell the witness to try again. This contrasts with another interrogating option of using a neutral interview technique, which includes both the bad and good aspects of the perpetrator.

Neither of these techniques is considered to be ethically sound for reasons similar to those provided by Bill Franke in the comments in respect to entrapment.

In addition to Jim's penetrating and pointed, you could also use the word probing to describe the questions asked during an interrogation.

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+1 for loaded questions. I was looking for that, but it totally eluded me. –  user21497 Jan 28 '13 at 8:34
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I would say he is asking penetrating or pointed questions.

penetrating : Keenly perceptive or understanding; acute

pointed : cutting or incisive

Or for a more poetic take on it:

His line of questioning laid out an impenetrable minefield for the guilty.

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