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Investigating students' reasoning while solving organic chemistry problems often includes the way in which students' prior knowledge affects their conceptual understanding of core organic chemistry concepts. Therefore, constructing rich and complex mental models (i.e., conceptual structures) and organized knowledge is an important goal for organic chemistry teaching and learning. The lack of understanding that results in misconceptions the students have integrated into existing mental models. This can guide and/or limit the students' mechanistic reasoning as they provide answers and explanations that differ from accepted theories in the domain. Evidence shows that traditional paper-and-pencil tests might not provide proper information about students' reasoning, conceptual understanding and/or lack of understanding in organic chemistry. Therefore, this chapter looks at a relatively new diagrammatic assessment approach: student-generated systemic synthesis questions. These questions could not be solved mechanically by applying previously learned algorithms. Therefore, they could help students to develop conceptual understanding. This assessment technique presents modified cyclic concept maps as students are required to draw the closed framework of noted concepts and to provide proper relationships among them by drawing marked arrows with the correct orientation. Examples of the student-generated systemic synthesis questions (in the form of drawings) will be offered in this chapter, showing guidelines for their interpretation and evaluation.

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