Esterification of an unknown alcohol. Identify starting alcohol and product. Show structure.

10.0ml of unknown

15.0ml of acetic acid

1.0ml of sulfuric acid

trolled by a Variac drying tube. The flask is heated by a heating mantle con Glass wool for cotton) ESSEN Drying tube Water out Water-cooled condenser Refuring Water in 50-ml round bottom flask To variac Heating mantle a Figure 18.1 Reflux assembly. 3. Turn on the water spigot and adjust to a slow flow of water. Bring the mixture to a gentle boil so that the "reflux ring" is no more than half-way up the condenser. Continue heating at reflux for 60 min 4. At the end of the reflux, remove the heating mantle and allow the system to cool to room tem- perature Isolation 1. Remove the reaction flask from the reflux assembly. Slowly add 15.0 ml of 5% aqueous sodium bicarbonate. Swirl the mixture to facilitate gas evolution a 2. When gas evolution slows, transfer the solution to a 125-mL separatory funnel (see Fig. 6.1. Pg. 59, for technique). Shake gently and vent occasionally by opening the stopcock, until there is no longer any gas evolution. Place the separatory funnel on a ring clamp (see Fig. 6.2, pg. 59) and allow to stand for 5 min. before drawing off the lower aquees ler. Add a fresh 15.0 mL of 5% aqueous sodium bicarbonate, shake and vent as before. Again draw off the lower layer after the layers have separated. Repeat with an additional 15.0 ml of 5% aqueous sodium bicarbonate 197.09 47.61 373.75 OPPM 3 PPM 2 PPM 1 PPM 4 PPM Unknown Alcohol 1.98 3.12 1.00 -C 2.5 PPM 2 PPM 1.5 PPM 1 PPM 0.5 PPM O PPM 3.5 PPM 3 PPM 5 PPM 4.5 PPM 4 PPM Unknown Product