The structure of Vitamin C (ascorbic acid) is shown below. As the name indicates, the molecule is somewhat acidic. Actually, one of the hydrogens on the four OH groups is much more acidic than the other three ones. Which one is the acidic hydrogen? Hints: To find the answer, you will again have to draw some resonance structures of the product formed after loss of H+. Consider the product after the loss of H+ for each of the OH groups. Only two of the OH groups have resonance structures after deprotonation; one of these two groups has a much better resonance structure than the other one (again after deprotonation). Note that the oxygen atom that is part of the five-membered ring has nothing to do with the problem.
Electronic Effects
The effect of electrons that are located in the chemical bonds within the atoms of the molecule is termed an electronic effect. The electronic effect is also explained as the effect through which the reactivity of the compound in one portion is controlled by the electron repulsion or attraction producing in another portion of the molecule.
Drawing Resonance Forms
In organic chemistry, resonance may be a mental exercise that illustrates the delocalization of electrons inside molecules within the valence bond theory of octet bonding. It entails creating several Lewis structures that, when combined, reflect the molecule's entire electronic structure. One Lewis diagram cannot explain the bonding (lone pair, double bond, octet) elaborately. A hybrid describes a combination of possible resonance structures that represents the entire delocalization of electrons within the molecule.
Using Molecular Structure To Predict Equilibrium
Equilibrium does not always imply an equal presence of reactants and products. This signifies that the reaction reaches a point when reactant and product quantities remain constant as the rate of forward and backward reaction is the same. Molecular structures of various compounds can help in predicting equilibrium.
The structure of Vitamin C (ascorbic acid) is shown below. As the name indicates, the molecule is somewhat acidic. Actually, one of the hydrogens on the four OH groups is much more acidic than the other three ones. Which one is the acidic hydrogen?
Hints: To find the answer, you will again have to draw some resonance structures of the product formed after loss of H+. Consider the product after the loss of H+ for each of the OH groups. Only two of the OH groups have resonance structures after deprotonation; one of these two groups has a much better resonance structure than the other one (again after deprotonation). Note that the oxygen atom that is part of the five-membered ring has nothing to do with the problem.
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