Assignment_8_Aldol_and_related_rxns

Assignment_8_Aldol_and_related_rxns - CHM 2120 Assignment 8...

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CHM 2120 – Assignment 8 In this assignment: - The aldol reaction - Haloform reaction - Synthetic applications Note : many questions incorporate earlier material 1. Draw the mechanism for the tautomerization of 1-phenyl-1-butanone (also known as butyrophenone and phenyl propyl ketone) under a. acid catalysis b. base catalysis Ph O Ph OH 2. a. What is the key tautomer of the molecule shown below? b. Which would be the major tautomer at equilibrium? Why? c. How could you prove the structure of the major tautomer by IR? O 3. a. Draw a mechanism for the generation of the compounds shown below. b. Describe how the 1 H NMR of the starting material would differ from the 1 H NMR of the two products. Note: H = 1 H Æ detected by 1 H NMR (peaks are seen) D = 2 H Æ not detected by 1 H NMR (no peaks) O NaOD D 2 O O O D D D 4. A solution of dimedone (5,5-dimethylcyclohexane-1,3-dione) in chloroform contains 33% of an enol tautomer. Draw this tautomer and explain why it is found in much higher proportion than most enols.
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This note was uploaded on 01/25/2011 for the course CHM 2120 taught by Professor Dr.flynn during the Spring '10 term at University of Ottawa.

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Assignment_8_Aldol_and_related_rxns - CHM 2120 Assignment 8...

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