Structural Formulae for Isomer P, Q and R: Explained

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Discussion Overview

The discussion revolves around identifying structural formulae for three isomers (P, Q, and R) based on their chemical behavior in reactions involving Cu(I) ions and manganate (VII) ions. The context includes aspects of organic chemistry, particularly related to oxidation reactions and the properties of carbohydrates.

Discussion Character

  • Exploratory
  • Technical explanation
  • Conceptual clarification
  • Homework-related

Main Points Raised

  • Isomer P likely produces a red precipitate due to the formation of cuprous oxide, suggesting it may be an aldehyde based on its reaction with ammoniacal cuprous solution.
  • Isomer Q is proposed to be ethanol, as it yields only ethanoic acid upon vigorous oxidation, indicating it does not undergo further oxidation to an aldehyde.
  • Isomer R is suggested to be a dicarboxylic acid, resulting from the oxidation of a dialcohol, although the exact structural formula is difficult to determine.
  • Some participants reference carbohydrates and suggest that the isomers may relate to sugars in their Fischer conformation.

Areas of Agreement / Disagreement

Participants express varying interpretations of the isomers' identities and their corresponding reactions, indicating that multiple competing views remain without a consensus on the exact structural formulae.

Contextual Notes

There are limitations regarding the assumptions made about the nature of the isomers and the specific reactions involved, as well as the unresolved details in determining the exact structural formulae for the aldehyde and dialcohol.

Who May Find This Useful

Students studying organic chemistry, particularly those focusing on oxidation reactions and carbohydrate structures, may find this discussion relevant.

MA103
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With an aqueous solution containing Cu(I) ions complexed by ammonia, isomer P gave a red precipitate. On vigorous oxidation by aqueous manganate (VII) ions, isomer Q gave only ethanoic acid whereas isomer R gave an unbranched chain, dicarboxylic acid.
Write structual formulae for isomers P, Q and R: explain your reasoning.

This is a past old examination question, I'm finding this difficult to answer. Anyone have any ideas?
 
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Hello, this is not an easy question, as you say.

The first one involving red precipitate is very likely to be cuprous oxide, Cu2O. This is an indicator of the positive Fehling test; and any oxidizable substance, but especially aldehydes. So ammoniacal cuprous solution is best reacted by an aldehyde; this is very similar to Tollens' test in which silver ions are used and a silver mirror is produced as a visual indicator.

The second one seems to be ethanol, since vigorous oxidation only gives the highest oxidation state; not the aldehyde stage, I think.

The last one is similar to the one before; but dialcohol is likely to be the solution of this problem.

It's difficult to draw the exact formulae for the aldehyde and dialcohol though.
 
I suggest that you go through the carbohydrates chapter in your organic chem text, this is what the question pertains to (glucose, fructose, mannose etc...).
 
GCT, you are a genius :smile:

Three isomers with one alcohol, one aldehyde and one dicarboxylic acid, involving Fehling test also are nothing but carbohydrates in Fischer conformation... I totally agree with you about this.
 

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