Download Exp 6 Williamson Ether Synthesis PDF

TitleExp 6 Williamson Ether Synthesis
TagsPerfume Ether Chemical Reactions Methanol Alcohol
File Size73.3 KB
Total Pages5
Document Text Contents
Page 3

KOH (MW= 56.11). Gently stir to completely dissolve the 2-naphthol. Move to the dispensing

hood and add 0.30 mL of iodoethane (MW 155.97, d= 1.940) with a graduated pipette. Cap the

reaction vessel (make sure to have both white Teflon plug and cap) and tighten the cap with the

wrench. Label the top of your reaction vessel with your name on a piece tape. Make sure not to

cover the hole on the top of the vessel. Your TF will microwave your reaction for 10 minutes at

130 °C at 1200 W power setting.

At the end of the heating period, recover your reaction vessel from the microwave

turntable and let the reaction mixture cool. Spot a solution of the 2-naphthol standard (you can

do this while your reaction is in the microwave to save time) and spot your reaction mixture on a

TLC plate (see TLC plate below).


Add 5 mL of H2O to your reaction mixture and transfer to a falcon tube. Add 5 mL of diethyl

and shake well. Collect the top organic layer with a Pasteur pipette and repeat this step 2 more

times. Each time collect the top layer and combine the organic fractions. Add the diethyl ether

fractions to a large falcon tube and add 10 mL of 2 M NaOH in water. Shake well and discard

the bottom layer. Repeat one more time and remove the bottom layer. Add 10 mL of saturated

NaCl solution in water to the falcon tube and shake. Collect the top organic layer. Dry the

solution by adding Na2SO4 (~0.5 g). Filter the suspension through a small pipette with cotton in

it and collect the filtrate. Rinse the Na2SO4with 2 mL of diethyl ether and collect. Evaporate the

diethyl ether away by blowing air on the sample until a solid is obtained. Record the mass of

your product obtained.


Dissolve a small amount of your product in acetone and spot it on your TLC plate from before.

Run your TLC plate in 4:1 hexane:ethylacetate, which has been provided. Record your TLC

plate in your notebook and calculate the RF of your product and 2-naphthol for your postlab.


Obtain a mass of your purified product, TLC, IR, GC/MS (1 mg of product dissolved in 1.5 mL

of hexane) and NMR (CDCl3).

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