Anyone good with organic chem reactions? I find this one really interesting

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Discussion Overview

The discussion revolves around the reaction mechanisms and conditions involved in the formation of esters, specifically focusing on the esterification of isopropanol and acetic acid. Participants explore various aspects of the reaction, including the role of catalysts, equilibrium considerations, and potential boiling point issues.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • Some participants propose that the compound in question may be an ester, specifically mentioning 2-propanol acetate.
  • One participant corrects the molecular weight and density values provided earlier, suggesting a molecular weight of 102 g/mol and a density of 0.87 g/ml.
  • Another participant notes that the formation of the ester will be slow without a catalyst, specifically sulfuric acid, and discusses the equilibrium nature of the esterification reaction.
  • It is mentioned that Le Chatelier's principle is typically applied in the lab to favor product formation during esterification by manipulating reagent concentrations or removing water.
  • Concerns are raised about the boiling point of isopropanol and whether the mixture with acetic acid forms an azeotrope, which could complicate heating the reaction mixture to 100 C.

Areas of Agreement / Disagreement

Participants express various viewpoints on the reaction conditions and mechanisms, indicating that multiple competing views remain regarding the specifics of the esterification process and its practical implications.

Contextual Notes

Participants do not resolve the uncertainty around the equilibrium position for the esterification reaction or the potential azeotropic behavior of the mixture.

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TL;DR
If 100ml of heated acetic acid was mixed with 1L of heated 2-propanol, let’s say 75-100C. Will 2-propanol acetate form? If so, how much? And with no addition of a strong acid like sulfuric acid or the high temperature, variables typically applied during esterification reactions. Answers don’t have to be exact. Interesting to see why ppl seem to get quite dissimilar answers though.
132g/ml
870g/mol
2-propanol acetate
 
Chemistry news on Phys.org
Correction:
102g/mol
Density .87g/ml
 
As a first guess, maybe an ester, like you did,
but if you want an expert, then someone else should also respond.
 
Formation of the ester will be very slow without a catalyst (which is what sulfuric acid is). Also, esterification is in equilibrium with the reverse reaction (ester hydrolysis to alcohol/carboxylic acid), and I don't know off the top of my head where that equilibrium sits for isopropanol and acetic acid. Typically when you do an esterification in the lab, you use Le Chatelier's principle to push the equilibrium toward products (either by adding one reagent in excess or by removing the water generated by the condensation reaction).
 
Also, isopropanol boils at around 80 C. I don't know whether the mixture of isopropyl and acetic acid forms an azeotrope. This will be an issue if you're heating the system up to 100 C.
 

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