Exp. 47 Postlab Rubric 2020_revised_with_exp_data
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Experiment 47: Synethesis of Dimedone and Measurement of Its Tautomeric Equilibrium Constant - Postlab Rubric
Postlab: 20 Points 1) Name, Section Number, Experiment Number, Title, and Date 2) Data and Results:
Describe the physical appearance and state of your product. See recitation slides.
Report the mass and percent yield of your product, showing calculations. mass = 1.81 g
Report your measured melting point/range and compare it to the literature melting point of the product. measured
mp = 146-148 o
C
Attach 1
H NMR spectra of the product in three different solvents (DMSO-d6, chloroform-d, and acetone-d6) with all signals assigned and labeled (excluding baseline/solvent impurities). On each 1
H NMR spectrum, draw the keto and enol tautomers and indicate whether each signal belongs to the keto or enol tautomer. If only the signals of one tautomer are visible, draw only this tautomer on the 1
H NMR spectrum. (See pp. 408-409 in Lehman for specific chemical shift values.) 3) Discussion and Conclusions
Did you achieve the objective of the experiment? Assume the experiment was successful.
Discuss whether or not your synthesis was successful and purification by recrystallization gave a pure product as evidenced by the melting point. Make sure to compare your melting point to the literature value.
Interpret all peaks in the three 1
H NMR spectra (except baseline/solvent impurities) and discuss whether or not the spectra confirm the identity and purity of the product.
Use the ratio of integrations of appropriate 1
H NMR peaks to calculate the tautomeric equilibrium constant (
K
) of dimedone in each of the three solvents.
Use the structures of the solvent to explain the differences in the equilibrium constant.
Discuss the product yield and any possible sources of loss of product that might be improved.
Draw a conclusion regarding the identity and purity of the product and discuss any possible sources of error. For example, if you obtained a large melting range, discuss possible reasons
for this outcome and any suggestions for improvement.
4) References
Include all references in the appropriate format, including the Lehman text. 5) Exercises
Answer questions 3, 7 and 10 (Lehman, p. 413).
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