Formation of the acid chloride will be done using a 100-mL round-bottom flask (RBF) with stir bar. Make sure that the glassware used is dry. Stick a wad of glass wool on the top of the condenser to trap some of the HCl; do not pack glass wool tightly, as it becomes restricted to gas flow. Not all of the HCl will be trapped, so keep the hood sash closed when doing this reaction.

After assembling the glassware, add 1.02–1.10 g of m-toluic acid to the 100-mL RBF. Add a magnetic stir bar to the RBF, and dilute/dissolve the solid with 5–7 mL of ether by stirring. Attach a Claisen adapter, and attach the condenser to one of the openings. Attach a rubber septum to the other opening.

Add 1.1–1.2 mL of thionyl chloride to the 100-mL RBF using a 5-mL syringe with a needle. Heat the mixture (heat controller at 30-45%) for 20–30 minutes at reflux. The reaction will produce HCl and SO2 gas. The reaction is complete once the evolution of gas stops.

After the evolution of gas has stopped, remove the heating mantle from the reaction assembly. If a cool hot plate is available, switch hot plates. Let the reaction cool to room temperature (approximately 5–10 minutes).

Part B: Formation of Amide

While the reaction is cooling to room temperature, prepare a mixture of N,N-diethyl amine and anhydrous ether; 2.5–2.6 mL amine and 2 mL ether. The amount of liquid should be enough to fit in a 5-mL syringe.

After the reaction mixture has cooled to room temperature, add 10–15 mL of ether through the rubber septum of the Claisen. Alternatively, the rubber septum may be removed and the ether added quickly.

Using a 5-mL syringe, insert the syringe into the reaction flask via the septum. Slowly add the amine/ether solution to the reaction mixture. Do this over a 20-minute period of time. Do not allow the boiling to become too vigorous. Allow the white cloud that forms with each addition to settle before making further additions. After the addition is complete, stir an additional 10–15 minutes.

Once the addition of the amine is complete, carefully remove the condenser and slowly add 15 mL of 5% Sodium Hydroxide through the Claisen into the reaction flask. Add the base slowly enough to minimize the white vapors of HCl formed. Once vapors are minimized, remove the Claisen adapter.

Stir the reaction RBF, and if required, agitate manually to completely dissolve all the solids once the vapors have subsided. Using pH paper, check the pH of the aqueous (aq) layer. If the pH is not 14, slowly add more of 5% Sodium Hydroxide until it is. Once the pH is 14, add 0.2–0.5 mL of N,N-diethyl amine and stir the RBF vigorously for 15–20 minutes.

Pour the contents into a separatory funnel. If too much of the ether has evaporated to see a distinct layer, add a little additional ether. Separate the lower aq layer. Add 5 mL of 5% Sodium Hydroxide, shake and separate the layers. Discard the lower aq layer.

Wash the reaction mixture ether layer with 10 mL of 10% hydrochloric acid, shake, and separate the layers. Discard the lower aq layer.

Wash the ether layer with 10 mL of saturated sodium chloride, shake and separate the layers. Discard the lower aq layer.

Dry the resulting ether layer with anhydrous sodium sulfate.

Decant the ether solution to an Erlenmeyer flask with stir bar, record the mass, and evaporate the ether with heating. Once all of the ether has been removed, obtain an accurate mass of the product.

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