1Chemistry 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 NCH3CH2OH23. 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 thefollowing synthesis could be carried out:CH2H2CH2COHCH2OH2CCH235. Methyl iodide is reacted with an unknown compound (“A”) to give a new compoundwith molecular formula C4H11N. The 1H NMR spectrum of the product “B” is givenbelow.(a) Give the structures of reactant “A” and product “B”.(b) Assign the 1H NMR resonances in the below spectrum to the hydrogens incompound “B”. The coupling information is:1.1 ppm – t, 3H2.2 ppm – s, 6H2.4 ppm – q, 2H46. A biochemically important compound has the molecular formula C5H6O5. Given thebelow spectra, determine the structure of the compound.2.5 ppm: triplet, 2H3.0 ppm: triplet, 2H13.0 ppm: broad singlet, 2H57. Compound A (C8H18O) undergoes a reaction to produce compounds B and Cin a 1 : 1 ratio:A BC+C8H18OCompound B has been analyzed by mass spectrometry, IR, 1H, and 13C NMRspectroscopy; the spectra appear below. Compound C has been analyzed by IR, 1H, and13C NMR spectroscopy; the spectra appear below. Determine the structure of A, B, andC, as well as an appropriate reagent for the transformation.B67. continued1H NMR:0.92 ppm – d, 6H1.75 ppm – m, 1H2.07 ppm – s, 1H3.39 ppm – d, 2H13C NMR:18.99 ppm30.84 ppm69.47 ppmBB77. continuedBC87. continued1H NMR:1.80 ppm – s13C NMR:36.44 ppm62.47
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