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My book has one example of the use of the second one; こうこうのとき, いいがくせいでしたか
which essentially is asking when you were in high school were you a good
student though i am confused why こうこう instead of こうこうせい but that is a whole
nother problem.

I doubt its as simple as one is a current tense and one is a past tense when.
perhaps one is the question when and the other is a time when?

I have no idea what to tag this please fix for me.
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english-to-japanese questions time
いつ and とき how to tell when to use which
You're on the right track. いつ is an interrogative, a question word. It's used
to ask when something happened or will happen, not to talk about a particular
time period. In English, we say:

> _When_ I was in high school.

In Japanese, it's:

> こうこうの _とき_

(There's nothing wrong with saying こうこうせいのとき; it's just a little less common,
probably because it's an extra word. In English, you can say, "Back in high
school" or "When I was in high school" or "When I was a high school
student...")

いつ and とき are never interchangeable. For example, you can say:

> じゅぎょうはいつですか。

When is the class? If you replaced いつ with とき, the sentence would make no
sense.
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These have different meanings:

**At this time, ...**

とき means “time” and can be used to state a time period. This is translated to
“when” in the sense of “at that time in which I was”

> 高校{こうこう}の **とき** 、〜
>
> **When** I was in high school, .... (In high school...)

Using 高校生{こうこうせい} or 学生{がくせい} for “student” is also acceptable.

> 高校生{こうこうせい}の **とき** 、〜
>
> **When** I was a high school student, ...

This can be used with a noun:

> 子供の **とき** 、〜
>
> **When** I was a child, ... (In my childhood...)

It can also be used with a verb or condition. In this case it’s usage is
similar to ら for “if”:

> お腹{なか}が空{す}いた **とき** 、〜
>
> **When** I am hungry, ...
>
> お腹{なか}が空{す}いた **ら** 、〜
>
> **If** I am hungry, ...

So 時{とき} is used to _state a time period_ in a subordinate clause, even if
that time period is hypothetical or hasn’t occurred yet.

**When?**

いつ is used to _ask a time period_ that the asker doesn’t know yet. いつ is only
used in questions. 「いつですか？」 means “when?” and is used in exactly the same way
for times as 「何{なん}ですか？」 for “what?”.

> 高校{こうこう}へ行{い}くのは **いつ** ですか？
>
> **When** are you going to high school?

Note that いつ and とき have different usage and cannot be used interchangeably.

**What time?**

いつ for “when?” and 何{なん}時{じ} for “what time” (what hour) can also be confused:

> 昼{ひる}休{やす}みは **[何]{なん}[時]{じ}** ですか？
>
> **What time** is (your) lunchbreak?
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