Monday, February 28, 2011 CHM 2211-0771 Quiz #07 Form BPage 1 of 1Please Last PRINTname:First name: UFID:______/20 pts. Put your answers in the spaces, or check Rԯor insert your answer 1.(8 pts) See Problem 19.46 For the retrosynthetic analysisof 3-phenylpropanoic acid, use the malonic estersynthesis. (a)Draw the structure of the precursor(ester) molecule. (b) Draw the structures of the starting materials. (c)For the actual synthesis starting from (b), provide the reagentsfor steps 1 and 2. (d)Provide reagentsand/or reaction conditionsfor steps 3, 4, and 5. COOHPh(a) Precursor (ester)(b) Starting materials+PhCH2BrStep 1:Step 2:HCl, H2O(c) Reagents for steps 1, 2EtONaStep 3:Step 4:Step 5:!HCl, H2ONaOH, H2O, !(d) Reagents, rxn conditions for steps 3, 4, and 5PhCO2EtCO2EtCO2EtCO2Et_____ 2.(7 pts) See Problems 19.50 (a)Draw curved electron arrowsto show how the enamine reacts with the α,βunsaturated ketone. (b)Draw (complete) the structure of the resulting first-formed intermediate
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