Chapter 3, Problem 44P

${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{SH}+{\text{CH}}_{\text{3}}{\text{O}}^{-}\to A\left(\text{contains sulfur}\right)+B$

$\to C\left(\text{which has the partial structure }A-{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{O }\right)$

$C+{\text{H}}_{\text{2}}\text{O}\to D+E\left(\text{which is inorganic}\right)$

(a) Given the above sequence of reactions, draw structures for A through E.

(b) Rewrite the reaction sequence, showing all nonbonding electron pairs and using curved arrows to show electron pair movements.