Recent advancements in machine learning have started to put their mark on educational technology. Technology is evolving fast and, as people adopt it, schools and universities must also keep up (nearly 70% of primary and secondary schools in the UK are now using tablets for various purposes). As these numbers are likely going to follow the same increasing trend, it is imperative for schools to adapt and benefit from the advantages offered by technology: real-time processing of data, availability of different resources through connectivity, efficiency, and many others. To this end, this work contributes to the growth of educational technology by developing several algorithms and models that are meant to ease several tasks for the instructors, engage students in deep discussions and ultimately, increase their learning gains. First, a novel, fine-grained knowledge representation is introduced that splits phrases into their constituent propositions that are both meaningful and minimal. An automated extraction algorithm of the propositions is also introduced. Compared with other fine-grained representations, the extraction model does not require any human labor after it is trained, while the results show considerable improvement over two meaningful baselines. Second, a proposition alignment model is created that relies on even finer-grained units of …