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Unformatted text preview: NAME: (please PRINT) Chemistry 1303
Exam I January 27, 1997 Q Value Total Score 3 @ 3 each (m4+4
(e) 7 (a) 9 x 3
(d) 1. Within each group of three, select by circling the strongest acid. <a> ANT M >L...
(C) Ongr O<HNH2 OgHOH II. Give the oxidation state at each starred carbon. (a) /\/*\S_S_© * (b) we. MeO OMe (C) WOW H1. The following two compounds, A and B, are isomeric. E." ‘3“3 5” 9H3
3' CH3 Br CH3 A B (1) Predict the number of signals in the proton NMR spectrum for each isomer. (2) Sketch the spectrum for isomer B. (3) Label your spectrum with an integration of peaks, reference standard, and approximate chemical
shifts. (4) How many peaks are expected in the proton-decoupled 13C NMR spectrum for A? (5) How could A and B be easily differentiated by NMR? IV. Starting with alkyne 1 below, provide the information requested for the
sequence shown. Br—E—O
l CuCl, base, 02
a/\_—> 1. n- -BuLi cat HgSO4
2. 1- Et 3 aq acid 1-13sz “Hz Na 1 NH
2 NaOH H202 Pd”331304 ——————3>
quinoline 1. 03, -78°
2. MezS, or
Zn/HOAc (a) Provide a structure for each of the products 2-10. Place answers in the boxes. (b) Provide a mechanism for the conversion of l to 3.
(0) Give the IUPAC name for 1. ((1) Assuming that the conversion of 3 to 6 involves a vinyl anion intermediate (HINTI), draw a 3D
orbital picture of such a species, in generic terms. ...
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