Chapter SRP, Problem 20P

The tranquilizing drug meprobamate (Equanil or Miltown) can be synthesized from 2-methylpentanal as follows. Give structures for meprobamate and for the intermediates A –C:

$\stackrel{\text{HCHO},{\text{HO}}^{-}}{\to }\left[\text{A}\left({\text{C}}_{\text{7}}{\text{H}}_{\text{14}}{\text{O}}_{\text{2}}\right)\right]\underset{{\text{HO}}^{-}}{\overset{\text{HCHO},}{\to }}\text{B}\left({\text{C}}_{\text{7}}{\text{H}}_{\text{16}}{\text{O}}_3\right)\stackrel{\text{ClCOCl}}{\to }$

$C\left({\text{C}}_9{\text{H}}_{\text{14}}{\text{Cl}}_2{\text{O}}_4\right)\stackrel{{\text{NH}}_3}{\to }\text{meprobamate }\left({\text{C}}_{\text{9}}{\text{H}}_{\text{18}}{\text{ O}}_{\text{4}}{\text{ N}}_{\text{2}}\right)$