instruction: Is the next sentence syntactically and semantically acceptable?

Many fish are in the sea.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

I know a man who Bill saw and liked Mary.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

You British or you Americans will get yourselves in trouble.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

With which club did you hit the winning putt?

response:
acceptable