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dehydration reaction (organic chem)

Anonymous Tue 01 Dec 00:44:05 2020 No.12405610 View Reply Original Report

Quoted By: >>12406117

if i add h2so4 (and heat) will this reaction happen? Or will an alkene form? there is a nitrogen next to the alcohol, so i'm not sure as to where the carbocation would form if at all

Anonymous

Anonymous Tue 01 Dec 2020 01:23:38 No.12405702 Report

Quoted By: >>12405958 >>12406117

Not sure if this will work but what I would do is protect the =O groups and reduce to an amine with Zn+HCl

Anonymous

Anonymous Tue 01 Dec 2020 02:35:32 No.12405958 Report

Quoted By:

>>12405702
thank you for your input anon :)

Anonymous

Anonymous Tue 01 Dec 2020 03:44:43 No.12406117 Report

Quoted By: >>12406306

>>12405610
as written that's not a dehydration, it's a deoxygenation (reduction).
>>12405702
brb checking Green's for protective groups for the sulfuryl.

OP should just reduce the hydroxamide and sulfuryl at the same time, then reoxidize at S.

Anonymous

Anonymous Tue 01 Dec 2020 04:43:40 No.12406306 Report

Quoted By:

>>12406117
>OP should just reduce the hydroxamide and sulfuryl at the same time, then reoxidize at S.

thank you for your input!
I was thinking my h2so4 idea to remove the alcohol group was too easy

Anonymous

Anonymous Tue 01 Dec 2020 07:44:36 No.12406669 Report

Quoted By:

h2so4 pronates -oh forming -oh2+ , electrons on nitrogen form the double bond kicking off h2o, what is attacking the =nh to form -nh2?

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