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BBBBCCCChemistry 2212 Organic Chemistry II Spring 2003Chemistry 2212 Organic Chemistry II Spring 2003Practice Midterm: covering material through the end of Chapter 131. Fill in the missing organic reagents for the following transformations:(a)NaHO(b)1. Mg, ether2. 3. H+OCH3CH2CHCH2CH2OHCH32. Predict the major organic product for the following transformations:NaOCH2CH3CH3CH2OH(a)Br1. TsCl/pyridine2.(b)C NCH3CH2OH13. Fill in the missing organic reagents for the following transformations:(a)OHCH2CH3HHCH3OCH2CHCH2CH3OH(b)CuLiLi24. Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with no more than two carbon atoms, indicate how the following synthesis could be carried out:CH2H2CH2COHCH2OH2CCH225. Methyl iodide is reacted with an unknown compound (“A”) to give a new compound with molecular formula C4H11N. The 1H NMR spectrum of the product “B” is given below.(a) Give the structures of reactant “A” and product “B”.(b) Assign the 1H NMR resonances in the below spectrum to the hydrogens in compound “B”. The coupling information is:1.1 ppm – t, 3H2.2 ppm – s, 6H2.4 ppm – q, 2H36. A biochemically important compound has the molecular formula C5H6O5. Given the below spectra, determine the structure of the compound.2.5 ppm: triplet, 2H3.0 ppm: triplet, 2H13.0 ppm: broad singlet, 2H47. Compound A (C8H18O) undergoes a reaction to produce compounds B and C in a 1 : 1 ratio:A BC+C8H18OCompound B has been analyzed by mass spectrometry, IR, 1H, and 13C NMR spectroscopy; the spectra appear below. Compound C has been analyzed by IR, 1H, and 13C NMR spectroscopy; the spectra appear below. Determine the structure of A, B, and C, as well as an appropriate reagent for the transformation. 5B7. continued 1H NMR:0.92 ppm – d, 6H1.75 ppm – m, 1H2.07 ppm – s, 1H3.39 ppm – d, 2H13C NMR:18.99 ppm 30.84 ppm 69.47 ppm 6BB7. continued 7BC7. continued 1H NMR:1.80 ppm – s13C NMR:36.44 ppm 62.47 ppm


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Villanova CHM 2212 - Practice Midterm

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