Wednesday, August 23, 2017

organic chemistry - If glucose can react with phenyl hydrazine to form osazone why can't it react with 2,4-DNP to give positive test?



If glucose can react with form phenyl hydrazine to form osazone why can't it react with 2,4-DNP?



Yes I know about cyclic form of glucose and its equilibrium with straight chain and all …


I read this, this and this Stack Exchange one too Does glucose react with Brady's reagent?


Still, didn't get an answer to my question. So requesting for clarification …



Answer




Glucose itself keeps interconverting between alpha beta glucopyranose and the chain form but it is more stable in this ring forms. A reagent should be strong enough to convert cyclic structure to the chain form so as to react with aldehyde group. I think due to electron withdrawing action of the Nitro groups in DNP they are less active/weaker than phenyl hydrazine and so DNP shouldnt convert glucose to chain form and react with the aldehyde. That's my explanation though.Someone might post a better answer.


No comments:

Post a Comment

periodic trends - Comparing radii in lithium, beryllium, magnesium, aluminium and sodium ions

Apparently the of last four, $\ce{Mg^2+}$ is closest in radius to $\ce{Li+}$. Is this true, and if so, why would a whole larger shell ($\ce{...