Acid 90

Acid
Charge a 25 mL r.b. flask fitted with a stir bar with 2.6 mL of acetic anhydride and 100
mg of *ZnCl2. Fit with a reflux condenser, and heat gently until the catalyst dissolves.
Slowly add 0.50 g of D-glucose in 2 increments (remove the condenser for each addition)
and stir between additions. Reflux the mixture in a water bath held at the temperature
assigned to you (+3C) for 1.5h. Timing begins when the first 250 mg of glucose have
been added.

Allow the reaction mixture to cool somewhat and then quench by pouring the reaction
solution slowly into a beaker containing 30-40 mL of a crushed ice/water mix. Stir well.
Transfer the entire reaction solution to a separatory funnel and add 25-30 mL of ethyl
acetate. Shake well, vent, and allow the layers to separate. Drain off the aqueous layer
and set it aside. Extract the organic layer with saturated sodium chloride (brine) solution
and then twice with water. Transfer the organic layer to an E. flask and dry it over
anhydrous sodium sulfate. Filter the dried solution into a clean, tared r.b. flask and
remove the solvent by rotovap. Vacuum dry the crude product. Obtain a weight and
calculate yield. Run tlc on the product. A good solvent should be neat ethyl acetate.
Visualize as described for the glucose procedure.

Glucose melting point

98-102

Mannose melting point none duh

Glucose rf values

Mannose rf valuses

Glucose final weight

.6256

mannose rb weight 56.029

57.1903