Question
Dichlorocarbene can be generated by reacting chloroform and aqueous sodium hydroxide in the presence of one of these species, where it acts as a phase transfer catalyst. For 10 points each:
[10m] Name these nitrogen-containing species. One of these species is formed as an intermediate in the Hoffman elimination by exhaustive methylation, before thermally decomposing into an alkene.
ANSWER: quaternary ammonium salts [or quaternary ammonium compounds or quaternary amines; accept quaternary ammonium cations; accept quats]
[10h] Quaternary ammonium salts are examples of these compounds, which include trimethylglycine. In general, these compounds are characterized by a positively charged functional group that bears no hydrogen atom adjacent to a negatively charged functional group.
ANSWER: betaines [prompt on zwitterions; prompt on ylides]
[10e] Oxaphosphetane likely does not form from a betaine intermediate in this reaction. This reaction uses a phosphonium ylide to convert carbonyls to alkenes.
ANSWER: Wittig reaction
<Science - Chemistry>
Summary
| 2024 ARGOS @ Brandeis | 03/22/2025 | Y | 3 | 6.67 | 33% | 33% | 0% |
| 2024 ARGOS @ Chicago | 11/23/2024 | Y | 6 | 16.67 | 100% | 50% | 17% |
| 2024 ARGOS @ Christ's College | 12/14/2024 | Y | 3 | 6.67 | 67% | 0% | 0% |
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| 2024 ARGOS @ McMaster | 11/17/2024 | Y | 5 | 14.00 | 80% | 40% | 20% |
| 2024 ARGOS @ Stanford | 02/22/2025 | Y | 3 | 23.33 | 100% | 100% | 33% |
| 2024 ARGOS Online | 03/22/2025 | Y | 3 | 16.67 | 100% | 33% | 33% |
Data
| Grzegorz Brzęczyszczykiewicz | Defying Suavity | 0 | 0 | 10 | 10 |
| Cambridge | Limp Franceskit | 0 | 0 | 0 | 0 |
| Simple Vibes | Cien Años de Quizboledad | 0 | 0 | 10 | 10 |