instruction: Is the next sentence syntactically and semantically acceptable?

Odysseus attempted the helmsman to hear the sirens.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

I should not eat plums.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

This key won't open the Jock.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

They know if Mary won.

response:
acceptable