the man that

[navi tasan]

Are these sentences correct:

1-We need a leader that when there is trouble people will trust him.
2-This is a machine that if you push any of its buttons a drink will flow from it.
3-That was the man that we did not know why he was given a medal.

Gratefully,
Navi.

[emsr2d2]

Are these sentences correct:

1-We need a leader that when there is trouble people will trust him.
2-This is a machine that if you push any of its buttons a drink will flow from it.
3-That was the man that we did not know why he was given a medal.

Gratefully,
Navi.

No.

1. We need a leader [who] people will trust when there is trouble.
2. This is a machine that/which dispenses a drink when you push any button.

Sentence 3 is actually quite hard to construct:

He is the man who was awarded a medal but no-one could understand why.