Does glucose in its cyclic structure react with HI ?

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The discussion centers on the reaction of glucose in its cyclic structure with hydrogen iodide (HI) and whether it can produce n-hexane (CH3-CH2-CH2-CH2-CH2-CH3). It is noted that the open-chain structure of glucose could potentially react with HI to yield n-hexane, but there are significant challenges. The conversation highlights that breaking O-C bonds and removing hydroxyl groups would be necessary for this transformation. However, a key point made is that the energy required for this reaction is substantial, approximately 1.25 megajoules per mole, indicating that the process is energetically unfavorable without additional energy input. While HI alone is insufficient as a reducing agent, the introduction of heat could facilitate the conversion of glucose into other organic molecules, although practical considerations such as yield and cost are significant barriers, similar to the impracticality of synthesizing gold from lead.
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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