Comparing Industrial Amination Reactions in a Combined Class and Laboratory Green Chemistry Assignment
Bibliographic record
Abstract
This article describes a comparative assignment developed for a third-year undergraduate organic synthesis course involving a combined laboratory experiment and class exercise. In this assignment, students compare the sustainability of two industrial amination reactions to form the same target molecule (4-( n- hexylamino)benzonitrile): a nucleophilic aromatic substitution procedure (S N Ar) provided in the class exercise, and a Buchwald–Hartwig (B–H) amination procedure completed in the laboratory. The assignment is structured using a “case-study” format to provide appropriate context. Students use industrial solvent and reagent substitution guides, complete process mass intensity calculations, and apply the Twelve Principles of Green Chemistry to compare and contrast the S N Ar and B–H reactions. They finally recommend a preferred reaction procedure after considering multiple sustainability concepts in their analyses. The assignment is highly adaptable as different industry guides may be used and the S N Ar reaction procedure is easily modified. Ultimately, students learn to apply sustainable chemistry principles to industrially relevant reactions, an important skill for their future careers.
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How this classification was reachedexpand
Full frame machine prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.
Distilled classifier scores by category (both heads)
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.005 | 0.011 |
| Meta-epidemiology (narrow) | 0.002 | 0.001 |
| Meta-epidemiology (broad) | 0.001 | 0.001 |
| Bibliometrics | 0.001 | 0.001 |
| Science and technology studies | 0.002 | 0.001 |
| Scholarly communication | 0.002 | 0.001 |
| Open science | 0.003 | 0.003 |
| Research integrity | 0.002 | 0.002 |
| Insufficient payload (model declined to judge) | 0.016 | 0.004 |
Machine scores (provisional)
The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.
Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.
score_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from itClassification
machine, unvalidatedMachine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.
How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".