instruction: Is the next sentence syntactically and semantically acceptable?

The more obnoxious Fred is, the less attention you should pay to him.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

I deny that that Bob has some money is certain.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

You and I are as much alike as a horse and a cow.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

He was hoping for more than we offered.

response:
acceptable