How do i get the context of a sentence?

How do i get the context of a sentence?

There is a questionnaire that we use to evaluate the student knowledge
level ( We do this manualy, as in a test paper ). It consist of the
following parts:

Multiple choice
Comprehension Questions ( i.e: Is a spider an insect? )
Now i have given a task to make an Expert System that will automate this.
So basically we have a proper answer for this. But my problem is the
Comprehension Questions. I need to compare the context of their answer to
the context of the correct answer.

I already initially search for the answer but it seems like it's really a
big task to do. What i have search so far is i can do this through NLP
which is really new to me. Also it seems like that i have to find a
dictionary of all words that is possible for the examiner to answer. This
is if i'm not mistaken.

Q: am i on the right track? If no please suggest of what should i do (
study what? ) or give me some links to the materials that i need. And also
should i make my own dictionary because the word that i will be using is
Filipino Language

If my question is not clear please say so, so i can provide more
information and sorry for my bad english.