instruction: Is the next sentence syntactically and semantically acceptable?

Who did he expect who I was acquainted with to show up?

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

I made to settle the matter my objective.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

Henry wanted to marry Fanny.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

Fred kicked the ball behind the tree.

response:
acceptable