Python Programming has become commonly used among IT and non-IT engineers for a variety of applications such as data analysis, prototyping, web application systems, and embedded systems. It offers rich libraries and short coding capabilities. To further promote this useful language, a high-quality self-study tool has been strongly demanded, since it is still rare to open Python programming courses at universities. In this paper, we study the Grammar-concept Understanding Problem (GUP) for self-study of Python programming by novice students. A GUP instance consists a source code and a set of questions describing the definitions of grammar or library keywords appearing in the code. The correctness of the answer from a student is marked through string matching with the correct keyword. In this study, we selected 114 keywords and common functions, and made the corresponding questions for them. Then, we generated 24 GUP instances with 142 questions and assigned them to 9 students in Okayama University. The results confirmed the effectiveness of the proposal.