Download Experiment 7: Acidity of Alcohols Williamson Ether Synthesis of

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B. Williamson Ether Synthesis of Methyl Propyl Ether
Na Br
The first step in this synthesis is preparation of sodium methoxide by reaction of
anhydrous methanol with sodium metal. Anhydrous methanol (10 mL) is added to a
clean, dry 25 mL round bottom flask containing a stir bar. The flask is fitted with an air
condenser and a water cooled condenser as shown in Figure 1. About 10 mL of dry
xylenes is added to a clean, dry 50 mL beaker. The beaker containing the xylenes is
weighed on a balance in a fume hood. Small pieces of sodium metal (stored under
xylenes) are added to the beaker obtain a net weight of about 0.75 grams of sodium.
(Note: the weight of sodium doesn't have to be exact but should be in the range 0.60 to
0.90 grams.) The sodium pieces are carefully transferred from the beaker to the round
bottom flask containing methanol and allowed to completely react. The resulting
sodium methoxide solution is cooled to room temperature and 2.00 mL (2.41 g) of
bromopropane is added and the flask is fitted for fractional distillation as shown in
Figure 2. With the receiver flask cooled in an ice bath, the reaction mixture is distilled,
collecting as one fraction all distillate coming over below 50 oC. The product is weighed
to determine % yield and analyzed by 1H NMR.
Figure 1
Figure 2
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