This action might not be possible to undo. Are you sure you want to continue?
Monosaccharides, or simple sugars, are polyhydroxyaldehydes or polyhydroxyketones. In a solution, they exist in equilibrium as an open chained or cyclic hemiacetal structures. The cyclic forms exist in alpha and beta anomers (two stereoisomeric configurations). When a cyclic structure forms, a new chiral carbon is also formed which results in two configurations. In the experiment, crude b-d-glucose pentaacetate, a derivative of glucose and acetic anhydride, was produced. Anhydrous sodium acetate was used as the catalyst. The crude product was massed and the melting point was taken. Procedure: 0.9 g (5.00 mmol) of pulverized glucose and 0.5 g (6.09 mmol) of pulverized anhydrous sodium acetate were added to a 25 mL round bottom flask. Then, 5 mL of acetic anhydride and boiling chips were added. The mixture was refluxed with constant stirring for 1.5 hours. The solution was poured into a 250 mL beaker filled with 50 mL of ice cold water. The mixture was stirred continuously for 45 minutes. It was then Buchner filtered and the residue was massed and melting was taken. Table of chemicals: Chemical Glucose Anhydrous sodium acetate Acetic anhydride Water Crude β-D-glucose pentaacetate (product) Mechanism
Quantity 0.904 g 0.5 08 g 5 mL 50 mL 1.477 g
MW (g/mol) 180.16 82.03 102.09 18.01 390.34
the solution was a turbid. Some sample was lost when the round bottom flask mixture was transferred into the beaker.4097% from the experimental product of 1. it contained impurities. The mixture initially was a white damp solid at the bottom with a solution layer on top. Such impurities could have increased the mass of the product. murky brown. the solution turned a dark red-brown color. During refluxing. Anhydrous NaOAc was a white powder which had an unpleasant odor. Percent Yield: ( )( )( ) Results: The percent yield of the crude a-d-glucose pentaacetate was calculated to be 75. the solution was somewhat clearer with chunks of dark brown. After stirring. there was product remaining on the stir bar after filtration. The residue was a fine brown coco-like powder with large black chunks. thus lowering the purity of the . Upon addition to the water. Also. Since the product was crude.477 g and the theoretical yield of 1. the filtrate was clear with some orange-brown oil-like drops. so product was also lost there. grainy powder. After refluxing. Acetic anhydride was clear and colorless.Observations: Glucose was a white. After filtration.9586 g. the solution was a dark brown solution with dark black chunks.
1 degrees Celsius which is a lower and broader range than the actual melting point of 135 degrees Celsius. which would interfere with the homogenous intereactions of a-d-glucose pentaacetate trying to crystrallize out. A pure compound would have had a sharp point at which the entire compound melted. This is probably due to the presence of an impurity. This was confirmed by the low melting point. . The melting point range was determined to be 129. The product contained both alpha and beta-d-glucose pentaacetate.5-131. Impurities could be removed by recrystallizing the crude product.final product. such as water. The range is broader due to the impurity. This is energetically favorable resulting in a lower melting point.