Computer-based knowledge and computation systems are becoming major sources of leverage for multiple industry segments. Hence, educational systems and learning processes across the world are on the cusp of a major digital transformation. This paper seeks to explore the concept of an artificial intelligence and natural language processing (NLP) based intelligent tutoring system (ITS) in the context of computer education in primary and secondary schools. One of the components of an ITS is a learning assistant, which can enable students to seek assistance as and when they need, wherever they are. As part of this research, a pilot prototype chatbot was developed, to serve as a learning assistant for the subject Scratch (Scratch is a graphical utility used to teach school children the concepts of programming). By the use of an open source natural language understanding (NLU) or NLP library, and a slackbased UI, student queries were input to the chatbot, to get the sought explanation as the answer. Through a two-stage testing process, the chatbot’s NLP extraction and information retrieval performance were evaluated. The testing results showed that the ontology modelling for such a learning assistant was done relatively accurately, and shows its potential to be pursued as a cloud-based solution in future.