(Solved): \( .59 \) The structure of montelukast, an antiasthma drug, is shown here. (a) Use Table L.8 to ide ...

\( .59 \) The structure of montelukast, an antiasthma drug, is shown here. (a) Use Table L.8 to identify the most acidic and most basic sites in the molecule. (Although you won't find an exact match in structure, make a prediction based on analogy with similar groups in simpler molecules.) (b) Write the structure of the product formed by treating montelukast with one equivalent of sodium hydroxide. (c) Write the structure of the product formed by treating montelukast with one equivalent of \( \mathrm{HCl} \). TABLE \( 1.8 \) Acidity Constants \( \left(p K_{\mathrm{a}}\right) \) of Acids -For acid base reactions in which water is the solvent, the \( \mathrm{pK}_{\mathrm{a}} \) of \( \mathrm{H}_{3} \mathrm{O}^{+} \)is zero and the \( \mathrm{pK}_{\mathrm{a}} \) of \( \mathrm{H}_{2} \mathrm{O} \) is 14. Web collections of \( \mathrm{p} K_{\mathrm{a}} \) data include that of \( \mathrm{H} \). Reich (University of Wisconsin) at hitpsi//www.chem.wisc.edu/areas/reichpkatable/ "For acid base reactions in which water is the solvent, the \( \mathrm{pK}_{\mathrm{a}} \) of \( \mathrm{H}_{3} \mathrm{O}^{+} \)is zero and the \( \mathrm{pK}_{\mathrm{a}} \) of \( \mathrm{H}_{2} \mathrm{O} \) is \( \ 4 \). The Bronsted-Lowry approach involving conjugate relationships between acids and bases makes a separate basicity constant \( K_{\mathrm{b}} \) unnecessary. Rather than having separate tables listing \( K_{\mathrm{a}} \) for acids and \( K_{\mathrm{b}} \) for bases, the usual practice is to give only \( K_{\mathrm{a}} \) or \( \mathrm{p} K_{\mathrm{a}} \) as was done in Table 1.8. Assessing relative basicities requires only that we remember that the weaker the acid, the stronger the conjugate base and find the appropriate acid-base pair in the table.