instruction: Is the next sentence syntactically and semantically acceptable?

Carla poured the pitcher with lemonade.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

I've never seen a taller man than my father.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

many equipment is available.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

How tall a man did Sheila marry?

response:
acceptable