Investigation of the Regioselectivity of Alkene Hydrations for the Undergraduate Organic Laboratory
Why this work is in the frame
A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.
Bibliographic record
Abstract
Due to a lack of time and, thus, an inability to present every possibility in a chemical reaction, organic chemistry professors tend to present each reaction with a single outcome. In practice, this is clearly not the case. A first-semester, three-week laboratory experiment designed for undergraduate organic chemistry students is described in which students carry out the hydration of a monosubstituted alkene via two different reactions, a hydroboration/oxidation and an oxymercuration/demercuration, in the first two laboratory periods, and analyze the resulting product mixtures in the third week via gas chromatography (GC). Students gain hands-on experience with the GC instrument and compare the results of the two reaction types. Both reactions are carried out on the same alkene starting material, and the ratios of the primary alcohol (anti-Markovnikov) and secondary alcohol (Markovnikov) products formed in each reaction are calculated. Students write a formal report and discuss the regiochemistry of the reactions, identifying each reaction as either regiospecific or regioselective, depending upon their GC results and mechanistic interpretation.
Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.
Full frame distilled prediction
Teacher imitationNot calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.
Codex and Gemma teacher scores by category
| Category | Codex | Gemma |
|---|---|---|
| Metaresearch | 0.000 | 0.003 |
| 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 | 0.000 |
| Insufficient payload (model declined to judge) | 0.000 | 0.000 |
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 it