ass8 - CHM 2120 Assignment 8 In this assignment: - The...

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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 b detected by 1 H NMR (peaks are seen) D = 2 H b 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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ass8 - CHM 2120 Assignment 8 In this assignment: - The...

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