Machine Learning: Advice and Possible Cooperation

I am doing a project. The project is a a plugin to install in Moodle to aid Exploratory behaviour and creativity in learning. I need to use AI technologies such that the learner can start from unknown to learn programming. Then when the learner deviates, the system can suggest something (eg. have you tried this?) to give hint and return them to the path where he/she will arrive to the required solution. Thus, I am supposed to use python and other AI technologies to implement this. What is your advise?