8487-Q-07A-KEY - Monday, February 28, 2011 Please PRINT...

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Monday, February 28, 2011 CHM 2211-8487 Quiz #07 Form A Page 1 of 1 Please Last PRINT name: First name: UFID: ______ /20 pts. Put your answers in the spaces, or check R or insert your answer 1. ( 8 pts ) See Example 19.8 (b); Problem 19.34 (c) For the retrosynthetic analysis of cyclopentanone, use the Dieckmann condensation . (a) Draw the structure of the precursor (ester) molecule . (b) Draw the structures of the starting material . (c) For the actual synthesis starting from (b), provide the reagents for steps 1 and 2. (d) Provide reagents and/or reaction conditions for steps 3, 4, and 5. O (a) Precursor (ester) O (b) Starting material Step 1: Step 2: HCl, H 2 O (c) Reagents for steps 1, 2 EtO Na Step 3: Step 4: Step 5: ! HCl, H 2 O NaOH, H 2 O, ! (d) Reagents, rxn conditions for steps 3, 4, and 5 CO 2 Et CO 2 Et CO 2 Et _____ 2. ( 7 pts ) See Problems 19.50 (a) Draw curved electron arrows to show how the enamine reacts with the α , β unsaturated ketone. (b) Draw (complete) the structure of the resulting
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