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Promblem Set #01 - carbonyl functionality Please propose a...

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Chemistry 436 Professor Paul J. Hergenrother Spring 2009 University of Illinois, Urbana-Champaign Problem set #1 Due in class at 8 AM on Friday, January 30 Turn answers in on a separate sheet of paper. For additional problems (not to be turned in), please see textbook Chapter 17 Problems 24, 25, 26, 27, 28, 29-32, 34, 35, 37, 38, 40. 1) Below is shown the 1 H NMR spectra of a compound with the molecular formula C 4 H 8 O. a) Draw the structure of this compound. b) What is the name of this compound? c) Please indicate which peaks on the spectra correspond with which protons in your structure. Triplet with integration of 1 Triplet with integration of 3 Multiplet with integration of 2 Multiplet with integration of 2 2) The following compounds can be made in one step from starting materials containing a
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Unformatted text preview: carbonyl functionality. Please propose a synthesis of these compounds, providing a detailed mechanism for the reactions. O O O O OEt EtO OMe OMe a) b) c) d) 3) Draw out all products for the reactions below, and provide a relative ranking of the equilibrium constants. Why are they ranked that way? For the reaction with the lowest equilibrium constant, how can we drive this reaction in the forward direction? O H + 2 EtOH + 2 EtOH O O + HO OH 1 4) Please provide the reagents for a-f that would give the indicated products. Please give the name of the functional group formed in each product. OH OH O NEt O O HO C N a) b) c) d) e) f) 5) Please complete the following syntheses, drawing out all products along the route. O H OH O NH 2 OH O OH OH OH O a) b) c) d) e)...
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