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# PRE-LAB QUIZ for EXPERIMENT 27 Name 1. In Experiment 27, a modified Perkin reaction is performed....

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PRE-LAB QUIZ for EXPERIMENT 27 Name 1. In Experiment 27, a modified Perkin reaction is performed. The Perkin reaction is a carbonyl condensation reaction that is related to the Claisen condensation and aldol condensation. In this experiment, the reactants are benzaldehyde and 3-benzoylpropionic acid with sodium acetate and acetic anhydride as catalysts. Draw the structures of these compounds in the space below. benzaldehyde 3-benzoylpropionic acid acetic anhydride 2. The first step of the reaction is the formation of the mixed anhydride of acetic acid and 3-benzoylpropionic acid. Draw the structure of this mixed anhydride in the space. NOTE: Equation E27.3 on page 349 of the textbook shows the general reaction. mixed anhydride of acetic acid and 3-benzoylpropionic acid -HOA R! HP mixed anhydride aldehyde R! The mixed anhydride then reacts with the aldehyde as shown to produce the initial product of the reaction. On the other side of the page, draw the structure of the initial product (the product at the lower right of the diagram) when the starting materials are 3-benzoylpropionic acid and benzaldehyde. H1 H1 H- HT- R? O Figure E27.3 from Pedersen & Myers, pape 350. R! Initial product
3. Draw the initial product that is formed from the reaction of benzaldehyde and the mixed anhydride of 3-benzoylpropionic acid and acetic acid. (This is the molecule shown at the lower right of Figure E27.3 with appropriate R' and Rgroups.) The product drawn above is not the final product of the reaction. To understand what happens next, consider the carbonyl group of the ketone portion of the molecule. The ketone carbonyl group in the initial product can undergo keto-enol tautomerism. In this case, the enol form may be favored because it has more extended conjugation than the keto form. 4. Re-draw the initial reaction product with the keto group converted to an enol. The enol has two functional groups: it is an acid anhydride and an alcohol. Acid anhydrides react with alcohols to form esters. In this case, the two groups react to form a cyclic ester (a lactone) which is the final product of the reaction. (Acetic acid or acetate is also a product of the reaction.) 5. Draw the structure of the final product in the space at the right. NOTE: The product is a cyclic ester, a lactone. 6. You can perform some of the calculations before you start the experiment. a) The procedure for Experiment 27 asks you to weigh out approximately 1 mmol of benzaldehyde. What is the mass of 1 mmol of benzaldehyde in milligrams? b) The procedure for Experiment 27 asks you to weigh out approximately 1 mmol of 3-benzoylpropionic acid. What is the mass of 1 mmol of 3-benzoylpropionic acid in milligrams? c) The procedure for Experiment 27 asks you to weigh out approximately 1 mmol of sodium acetate (CH,COO Na*). What is the mass of 1 mmol of sodium acetate in milligrams?

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