The analgesic meperidine (Demerol) was developed in the search for analgesics with- out the addictive effects of morphine. As shown in these structural formulas, it repre- sents a simplification of morphine's structure. H.C. H,C. CH3 (redraw) НО OH Morphine Meperidine Meperidine is prepared by treating phenylacetonitrile with one mole of bis(N-2- chloroethyl)methylamine (a nitrogen mustard) in the presence of two moles of sodium hydride to give (A). Refluxing (A) with concentrated sodium hydroxide followed by neutralization of the reaction mixture with dilute HCl gives (B). Treating (B) with ethanol in the presence of one equivalent of HCl gives meperidine as its hydrochloride salt. N-CH, 1. NaOH C13H16N2 2 NaH 2. HCI (A) Phenylacetonitrile ELOH, HCI C13H1,NO, C5H2NO, · HCI (В) Meperidine hydrochloride
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.
Propose structural formulas for (A) and (B).
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