instruction: Is the next sentence syntactically and semantically acceptable?

The sooner you call, the more carefully I know a man that will word the letter.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

That monkey is ate the banana

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

the bottle drained the liquid free.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

He gave me more of his marbles than I wanted.

response:
acceptable