Does glucose in its cyclic structure react with HI ?

[leojun]

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)

 

[Adsit_Deus]

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.

 

[Bystander]

One and a quarter megajoules per mole of glucose says it doesn't.

 

[Adsit_Deus]

Could you explain why not?

 

[Bystander]

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.

 

[Adsit_Deus]

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?

 

[Bystander]

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.