529 - Practice Problem 5‐29 – Answer The following...

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Unformatted text preview: Practice Problem 5‐29 – Answer The following reaction involves an intramolecular Michael reaction followed by an intramolecular aldol reaction. Write both steps, and show their mechanisms. Practice Problem 5‐30 – Answer The following reaction involves a conjugate addition reaction followed by an intramolecular Claisen condensation. Write both steps, and show their mechanisms. O CO2CH3 (CH3)2CuLi CO2CH3 C C CO2CH3 CH3 Practice Problem 5‐31 – Answer The following synthetic route is used to prepare an intermediate in the total synthesis of the anticholinergic drug benzilonium bromide. Propose structures for A, B, C, and D. Practice Problem 5‐32 – Answer How might the following compounds be prepared using Michael reactions? Show the nucleophilic donor and the electrophilic acceptor in each case. (a) (b) (c) (d) (e) (f) Practice Problem 5‐33 (1st one) – Answer Show experimental conditions by which to carry out the following synthesis. Practice Problem 5‐33 (2nd one) – Answer What products would you expect from a Robinson annulation reaction of 2‐methyl‐1,3‐cyclopentanedione with 3‐ buten‐2‐one? Practice Problem 5‐34 – Answer How would you prepare the following compound using a Robinson annulation reaction between a β‐diketone and an α,β‐unsaturated ketone? Draw the structures of both reactants and the intermediate Michael addition product. ...
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This note was uploaded on 10/25/2010 for the course CH 310n taught by Professor Iverson during the Summer '08 term at University of Texas at Austin.

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