Question: The following experimental procedures are referred to in both Part A and Part B. This is a three step procedure for the synthesis of mesitylacetic acid 1 from mesitylene 2 (1,3,5-trimethylbenzene). Step 1: Chloromethylmesitylene 3. Mesitylene 2 (200 g, 1.66 moles), 1 L of concentrated hydrochloric acid (1 L), and formaldehyde solution (63 mL,0.84 mole) were

The following experimental procedures are referred to in both Part A and Part B. This is a three step procedure for the synthesis of mesitylacetic acid 1 from mesitylene 2 (1,3,5-trimethylbenzene). Step 1: Chloromethylmesitylene 3. Mesitylene 2 (200 g, 1.66 moles), $1\mathrm{L}$ of concentrated hydrochloric acid $(1\mathrm{L})$, and formaldehyde solution $(63\mathrm{mL},0.84$ mole) were placed in a round bottomed flask. Hydrogen chloride was introduced below the surface of the mixture through a gas inlet tube. The mixture was stirred vigorously and heated to keep the temperature of the mixture at $55-60^{\circ }\mathrm{C}$ for 5.5 hours. At the halfway point, additional formaldehyde solution ( $63\mathrm{mL},0.84$ mole) was added. After the mixture had been cooled to room temperature, it was extracted with ether $(3\times 300\mathrm{mL})$. The combined ether extracts were washed successively with water, dilute sodium hydroxide, and brine, dried over sodium sulfate, and filtered. The ether was removed and the residue was distilled under reduced pressure $\left(130-131^{\circ }/22\mathrm{mm}\right)$ to give chloromethylmesitylene $3(155-170$ $\mathrm{g})$; the distillate solidified to a crystalline mass ( $\mathrm{mp}37-38^{\circ }\mathrm{C}$ ). Step 2: Mesitylacetonitrile 4. A solution of sodium cyanide, $(66.2\mathrm{g})$ in water (110 $\mathrm{mL})$ and ethanol $(160\mathrm{mL})$ was heated at reflux until all the sodium cyanide had dissolved. Chloromethylmesitylene $3(152.5\mathrm{g},0.90$ mole) was then added slowly, and the heating was continued for 3 hours. The mixture was allowed to cool to room temperature and extracted with ether $(3\times 300\mathrm{mL})$. The organic extracts were washed with water, dried over sodium sulfate and filtered. After removal of the ether, the residue was distilled under reduced pressure (160$165^{\circ }/22\mathrm{mmHg})$ to give mesitylacetonitrile $4(128-133\mathrm{g})$ which solidified upon standing. Step 3: Mesitylacetic acid 1. Concentrated sulfuric acid $(750\mathrm{mL})$ was cautiously added to water $(900\mathrm{mL})$. When the mixture had cooled to about $50^{\circ }\mathrm{C}$, mesitylacetonitrile $4(127\mathrm{g},0.80$ mole) was added. The mixture was heated at reflux. A precipitate formed during heating. The contents of the flask were cooled and poured into ice water $(3\mathrm{L})$. The precipitate was collected on a Büchner funnel, washed well with acetone and