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Wednesday, January 29, 2020

Fructose contains a keto group, yet it reduces Fehling solution and Tollen's reagent. Why ?



Fructose although contains a ketone group yet it acts as a reducing sugar. This is explained by the formation of glucose from fructose by enolisation. Enolisation results in the formation of glucose from fructose and vice versa. (Lobry de Bruyn Van Ekenstein rearrangement).

There are two -NH2 groups in semicarbazide that might react with a ketone or aldehyde. Explain why the reaction occurs with only one -NH2.

The -NH2 group closer to the carbonyl group is deactivated (resonance-stabilized) compared with the other end -NH2 group:




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Tuesday, January 28, 2020

How does it account for benzene's extraordinary stability ? Give an orbiial picture of benzene ?



The ring is comprised of six sp2 hybridized carbon's each sigma bonded  to carbon’s and an H. (Fig-1) Each Carbon  also has a "p" AO with one electron :  the AO's project above and below the plane of the ring which is a nodal plane. Rather than form three localized alternating doubic bonds (cycIohexatriene). these "p" AO's overlap  laterally to form an extended π-system in which the electrons  are symmetrically delocalized over all six carbon's making the Carbon's equivalent . (Fig-2) Delocalization results in less electron repulsion, greater stabilizalion, and lower energy.