instruction: Is the next sentence syntactically and semantically acceptable?

Tom drives like that man.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

Both of the workers will wear carnations.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

Who was the book sent by John.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

How slowly would you say he was driving?

response:
acceptable