Chapter 3, Problem 3.107P

Aspirin (acetylsalicylic acid, ${\text{C}}_{\text{9}}{\text{H}}_{\text{8}}{\text{O}}_{\text{4}}$ ) is made by reacting salicylic acid $\left({\text{C}}_{\text{7}}{\text{H}}_{\text{6}}{\text{O}}_{\text{3}}\right)$ with acetic anhydride $\left[{\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ : ${\text{C}}_{\text{7}}{\text{H}}_{\text{6}}{\text{O}}_{\text{3}}\left(s\right)+{\left({\text{CH}}_{\text{3}}\text{CO}\right)}_2\text{O}\left(\text{l}\right)\to {\text{C}}_{\text{9}}{\text{H}}_{\text{8}}{\text{O}}_{\text{4}}\left(s\right)+{\text{CH}}_{\text{3}}\text{COOH}\left(\text{l}\right)$ In one reaction, 3.077 g of salicylic acid and 5.50 mL of acetic anhydride react to form 3.281 g of aspirin. (a) Which is the limiting reactant (d of acetic anhydride = 1.080 g/mL)? (b) What is the percent yield of this reaction?