abstract: In the last decade, the immense growth of computational power, enhanced data storage capabilities, and the increasing popularity of online learning systems has led to adaptive learning systems becoming more widely available. Parallel to infrastructure enhancements, more researchers have started to study the adaptive task selection systems, concluding that suggesting tasks appropriate to students' needs may increase students' learning gains. This work built an adaptive task selection system for undergraduate organic chemistry students using a deep learning algorithm. The proposed model is based on a recursive neural network (RNN) architecture built with Long-Short Term Memory (LSTM) cells that recommends organic chemistry practice questions to students depending on their previous question selections. For this study, educational data were collected from the Organic Chemistry Practice Environment (OPE) that is used in the Organic Chemistry course at Arizona State University. The OPE has more than three thousand questions. Each question is linked to one or more knowledge components (KCs) to enable recommendations that precisely address the knowledge that students need. Subject matter experts made the connection between questions and related KCs. A linear model derived from students' exam results was used to identify skilled students. The neural network based recommendation system was trained using those skilled students' problem solving attempt sequences so that the trained system recommends questions that will likely improve learning gains the most. The model was evaluated by measuring the predicted questions' accuracy against learners' actual task selections. The proposed model not only accurately predicted the learners' actual task selection but also the correctness of their answers. / Dissertation/Thesis / Doctoral Dissertation Computer Science 2020