Is the following sentence linguistically acceptable?
Tom tried for Bill to ask a question.

unacceptable

Is the following sentence linguistically acceptable?
I went out with a girl who that John showed up pleased.

unacceptable

Is the following sentence linguistically acceptable?
Mary should buy some flowers on Sunday at 5 o'clock.

acceptable

Is the following sentence linguistically acceptable?
He threw the letter into the wastebasket.
acceptable