Hydrolysis of ROH: Using HCl & ZnCl2 w/ Water

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Discussion Overview

The discussion revolves around the hydrolysis of alcohols (ROH) using hydrochloric acid (HCl) and zinc chloride (ZnCl2) as catalysts, specifically focusing on the differences in reaction conditions for primary, secondary, and tertiary alcohols. The scope includes mechanistic reasoning and experimental considerations.

Discussion Character

  • Exploratory
  • Technical explanation
  • Experimental/applied

Main Points Raised

  • One participant notes that dry HCl and anhydrous ZnCl2 are typically used for primary and secondary alcohols, questioning the appropriateness of using concentrated HCl and ZnCl2 with small amounts of water for tertiary alcohols.
  • Another participant suggests considering the mechanism of the reaction and the stability of the carbocation intermediate.
  • A participant proposes that the stability of the carbocation intermediate for tertiary alcohols means that the presence of a small amount of water does not significantly affect the reaction.
  • One participant inquires if the discussion is related to the Lucas test experiment, recalling that concentrated acid is added to all solutions and suggesting verification with the manual.

Areas of Agreement / Disagreement

Participants express differing views on the impact of water on the reaction mechanism, particularly regarding tertiary alcohols. The discussion does not reach a consensus on the appropriateness of using water in the reaction conditions.

Contextual Notes

Participants reference the stability of carbocation intermediates and the specific conditions of the Lucas test, indicating potential limitations in understanding the full implications of water's presence in the reaction.

Who May Find This Useful

Readers interested in organic chemistry, particularly those studying reaction mechanisms and experimental procedures involving alcohols and substitution reactions.

Clari
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In the substitution of ROH to RX, dry HCl and anhydrous ZnCl2 catalysts are used for primary and secondary alkanol. Why it is fine to use concentrated HCl and ZnCl2 for tertiary alkanol, that is to say, with small amounts of water present?
 
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Think about the mechanism of the reaction, and the trends in the stability of the intermediate
 
so because the carbocation intermediate of tertiary ROH is more stable, so the presence of a little amount of water does not affect the reaction much. Am I right? :rolleyes:
 
You're doing the lucas test experiment right? From what I remember, you're supposed to add concentration acid to all solutions, you might want to ascertain whether your manual indicates otherwise.
 

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