Relative pronoun and 的 troubles
I've learned that the relative pronoun doesn't really exist in Chinese, but is shown by 的. This is all easy to understand so far, but the word order when using it as a relative pronoun confuses me. I mean, I understand when reading it, but when making my own sentence I get confused. For example: 一点到五点走的男子很高兴 or is it 一点到五点的男子很高兴走? Or what about: 我看了的人 or 人的我看了？(side note I'm probably saying "from blank o'clock to black o'clock" wrong)
And I'm also a bit confused on when to use 的 with adjectives. I've read that one syllable adjectives go in front and two+ syllable adjectives go after and are connected by 的, but I've seen example where 的 is used no matter what. What are the rules for this?
As you didn't provide the English sentence it is not easy to judge whether you have successfully delivered your meaning. I can understand the sentence
[The man] [who] [arrived at 1] and [left at 5 ] was [very happy].
In this sense it is acceptable.
As to 一点到五点的男子很高兴走, I don't think it would be a good sentence by all means.
If you are not certain, you should try to make up the clauses first, and then rearrange them, to avoid making a deliberate word order.
→ 一点到五点走 的 男人 很高兴
→ 很高兴 的 男人 一点到五点走
I am not saying these sentences are all that natural, but I think at least there is no grammar issue.
I continue your choice of word for “To walk” as 走. If more context is given, other words may be better. Also 点 is for verbal use only. The written form should be 时. 2 o'clock in written form is 二时, but its verbal form is 两点.
To say "to walk from A o'clock to B o'clock" naturally in Chinese, we actually should put the verb in the middle:
It is not natural to to say 从A点到B点走. We only do that when we talk about a schedule.
Now it should be easy to translate "That man walked from 1 o'clock till 2 o'clock"
那个男人 从一点 走 到两点
Concerting to a clause it gives
→ 从一点 走 到两点 的 男人～