This study develops and evaluates an automated assessment model using Abstract Syntax Trees (AST) with a view to overcoming the limitations of string-matching techniques in the assessment of Fill-in-the-Blank (FIB) programming answers. Traditional string-matching techniques have a relatively high False Negative Rate (FNR) of 21.5% within the context of detecting semantic equivalence. The current model uses semantic structural triangulation to ascertain the semantic similarity of student answers. Technical assessment shows that the AST approach markedly reduces the FNR to 4.5%. The model demonstrates high reliability (ϰ = 0.83) with high classification accuracy (F1 Score = 0.966) which attests to its inferential validity. From a pedagogical perspective, system implementation leads to substantial learning gains, evidenced by a large effect size (Cohen’s d = 1.82) and a high normalized gain (Normalized Gain = 0.90). Multiple regression analysis confirms that semantic accuracy is the primary causal factor driving improved student comprehension. Ontologically, while AST is valid as a partial representation, its limitations—particularly tree isomorphism in recursive structures—highlight the need for further exploration of graph isomorphism approaches. Control Flow Graphs (CFG) and Data Flow Graphs (DFG) offer more expressive relational models for capturing control and data dependencies. The model demonstrates functional feasibility with a System Usability Scale (SUS) score of 76.47. Overall, the AST Triangulation Model is validated as pedagogically effective, inferentially robust, and supportive of evaluative transparency. Future research recommends validating the model on more complex tasks and releasing it as open-source to support reproducibility.
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