Optimization of the Synthesis of <i>n</i> -Phthalimidoalkylthiols as Precursors for ω-Aminoalkylthiols as Prepared by Undergraduate Chemistry Students
Bibliographic record
Abstract
The synthesis of n-phthalimidoalkylthiols from phthalimide and n,m-dibromoalkane was demonstrated as a general approach to short and medium chain (× = 1 to 12) functional alkylthiols in an undergraduate laboratory setting. The reaction conditions were demonstrated to be mild enough to directly synthesize n-phthalimidoalkylthiols with a carbon chain containing either double or triple bonds. The syntheses of each of these alkylthiols can be completed in less than 24 h (over a few laboratory periods) with at least a 50% overall yield. Reactivity of n,m-dibromoalkane with phthalimide was monitored with 1H-NMR to determine the length of time needed for the reaction to reach completion avoiding the inaccurate use of thin layer chromatography. Based on this result, reaction times were reduced by two-thirds from those previously reported in the literature, which was necessary to prepare a method that will accommodate the duration of second year introductory organic or organic spectroscopy courses.
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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 | 0.000 | 0.001 |
| Meta-epidemiology (narrow) | 0.000 | 0.000 |
| Meta-epidemiology (broad) | 0.000 | 0.000 |
| Bibliometrics | 0.000 | 0.000 |
| Science and technology studies | 0.000 | 0.000 |
| Scholarly communication | 0.000 | 0.000 |
| Open science | 0.000 | 0.000 |
| Research integrity | 0.000 | 0.001 |
| Insufficient payload (model declined to judge) | 0.002 | 0.001 |
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".