Discussion Overview
The discussion revolves around the reaction mechanism involved in converting acetaminophen to phenacetin using different alkyl halides (Ethyl iodide vs. 2-iodopropane) and how this choice affects the reaction velocity. Participants explore the nature of nucleophilic substitution reactions, specifically whether they follow an SN1 or SN2 mechanism, and the implications of using primary versus secondary alkyl halides.
Discussion Character
- Homework-related
- Debate/contested
- Exploratory
- Technical explanation
Main Points Raised
- One participant questions how the stability of the reaction with NaOH affects the reaction velocity, suggesting it might remain the same.
- Another participant seeks clarification on whether the nucleophilic substitution reaction is SN1 or SN2.
- Some participants assert that the reaction with Ethyl iodide is SN1 due to its two-step mechanism, while questioning if the same applies to 2-iodopropane.
- There is a discussion about the strength of 2-iodopropane as a nucleophile compared to Ethyl iodide.
- One participant describes the process of neutralization of the hydroxyl group in acetaminophen, leading to a negative oxygen that acts as a nucleophile.
- Another participant proposes that the reaction with Ethyl iodide might actually be SN2, prompting further exploration of the implications of using a secondary alkyl halide.
- Concerns are raised about the rate of SN2 reactions being influenced by the substrate and electrophile, particularly regarding stereochemical repulsion with 2-iodopropane.
- A later reply emphasizes that the rate of reaction depends on the substrate, leaving group, and attacking nucleophile, suggesting that the same leaving group and nucleophile in both cases should simplify the analysis.
Areas of Agreement / Disagreement
Participants do not reach a consensus on whether the reactions are SN1 or SN2, and there are differing opinions on the impact of using 2-iodopropane compared to Ethyl iodide. The discussion remains unresolved regarding the exact nature of the reaction mechanisms and their effects on reaction velocity.
Contextual Notes
Participants express uncertainty about the mechanisms involved and the factors affecting reaction rates, including the roles of nucleophiles and substrates. There are references to the need for further exploration of the topic in relevant texts.