Question

1) Analysis subquestions (7 points): (a) Draw the mechanism of the reaction - remember, there are two main parts to the aldol condensation, the addition step, followed by the elimination. (b) Explain why your reaction forms the enone product, rather than the hydroxyketone intermediate. 2) Critical analysis (7 points): a) You have been given a 1H NMR spectrum of your product. Fully assign this spectrum (i.e. determine which peaks in the 1H NMR correspond to which hydrogens in the product). The peaks have been labeled 1-8 on the spectrum, and the relevant hydrogens Ha-Hh below. b) Calculate the coupling constant between He and Hf. Explain how can this can help determine the stereochemistry (i.e. cis vs. trans) of the double bond. (7) Acetone is a symmetrical molecule, so there are two positions that can react. Draw the product you would expect to obtain if you used two molar equivalents of vanillin rather than one. c) Acetone is a symmetrical molecule, so there are two positions that can react. Draw the product you would expect to obtain if you used two molar equivalents of vanillin rather than one.

Answer 1

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