Does glucose in its cyclic structure react with HI ?

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Discussion Overview

The discussion centers around whether glucose in its cyclic structure can react with hydrogen iodide (HI) to form n-hexane. Participants explore the chemical reactions involved, including the potential reduction of glucose and the energy considerations associated with such transformations.

Discussion Character

  • Debate/contested

Main Points Raised

  • One participant questions if glucose in its cyclic structure reacts with HI to produce n-hexane, referencing the open chain structure's reaction with HI.
  • Another participant agrees that glucose could be reduced to n-hexane, suggesting that an O-C bond would break and hydroxyl groups would be removed, although they express uncertainty about the technical details.
  • A third participant argues against the reaction, citing a significant energy requirement (one and a quarter megajoules per mole) that suggests the reaction does not occur.
  • In response, a participant asks for clarification on the reasoning behind this claim.
  • Another participant elaborates that the reaction involves moving from a partially oxidized state to a fully reduced state, which requires energy that HI alone cannot provide.
  • One participant humorously suggests that energy input, such as heat, could change the outcome, while agreeing that HI alone is insufficient for reduction.
  • A later reply states that with enough energy, it is theoretically possible to convert various organic molecules into others, but practical challenges such as yield and cost would be significant.

Areas of Agreement / Disagreement

Participants express differing views on the feasibility of glucose reacting with HI to form n-hexane, with some supporting the idea of reduction and others arguing against it based on energy considerations. The discussion remains unresolved with multiple competing perspectives.

Contextual Notes

Participants reference energy requirements and the nature of chemical transformations without fully resolving the underlying assumptions or providing detailed mechanisms for the proposed reactions.

leojun
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does glucose in its cyclic structure react with HI to form CH3-CH2-CH2-CH2-CH2-CH3?
(open chain structure of glucose reacts with HI to form CH3-CH2-CH2-CH2-CH2-CH3)
 
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I believe so, yes. I think that the glucose would be reduced and would give n-hexane.
It has been a while since I've looked at anything like this (which is bad since I have a final coming up), but I believe that an O-C bond would break and hydroxyl groups would lyse off from there. I know that that isn't very technical.
 
One and a quarter megajoules per mole of glucose says it doesn't.
 
Could you explain why not?
 
Why do rocks not rise into the air from a position of rest on the ground? You're pushing a partially oxidized carbon chain "uphill" to a fully reduced, higher energy state (~1.25 MJ/mole higher) with an extrememly weak reducing agent, HI. It does not work.
 
Unless you use a catapult. I agree that HI by itself will not reduce it, you are correct. With an input of energy (heat) though?
 
You can take (almost) any organic molecule as a feedstock and turn it into (almost) any other organic molecule with enough energy. Yield and expense will kill you, not unlike synthesizing gold from lead.
 

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