instruction: Is the next sentence syntactically and semantically acceptable?

How hard to read the book it was!

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

I am neither an authority on this subject nor trying to portray myself as one.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

Anne met Cathy.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

The man who ordered ice cream said the pudding would be tasty.

response:
acceptable