Tutor-marked Assignment 2 (Units 10-16)

Tutor-marked Assignment 2 (Units 10-16)Do the following tutor-marked assignment after you have finished workingon Unit 8. When you are satisfied with your answers, send the completedassignment to your tutor for grading. See the Student Manual forinformation about submitting your assignments for grading.1. Provide a complete IUPAC name for each of the following compounds.Assign stereochemistry (E/Z) and/or (R/S) where appropriate.a.BrClb.ClI444˜444 ˜ 4˜ 4˜4 ˜4 ˜c.IHClOrganic Chemistry I792. Starting with butane, explain how you could prepare:a. 2-bromobutaneb. 1-bromobutaneNote: For the following targets, you may also choose to begin witheither 2-bromobutane or the 1-bromobutane as prepared abovewithout repeatedly showing how you made these two compounds. Besure to choose the best starting material for each job!c. 1-butened.4˜ 4D4 ˜4e. 3-methylheptanef. 5-methyl-3-heptyne80Chemistry 350 / Assignment Manual3. Explain how you would prepare each of the following compounds frombenzene:a. phenolb. o-ethyltoluenec. 3-chloroanilined. p-nitrobenzoic acid4. Sketch the expected 1 H NMR spectrum for the following compound,doing your best to estimate and represent the chemical shift of eachproton, as well as the anticipated integrations and splitting patterns.4˜ 4O ˜44˜4 ˜ 4˜˜44˜ 444 4 ˜44444p-ethoxyphenylacetyleneOrganic Chemistry I815. For each of the following sets of reaction conditions, identify whichmechanism or mechanisms you expect to dominate: SN l, SN 2, El, or E2.Draw the major product or products you would expect to isolate ineach case.a.b.Ph4˜ 44 ˜4 OTos˜ 4 ˜4 Cl˜ 4˜ 4H2 OGGGGGGGGGAKOHGGGGGGGGGAEtOH4˜ 4˜ 4Br4 ˜ 4 ˜4˜˜c.4˜44˜482NaSCH3GGGGGGGGGGGGGADMFChemistry 350 / Assignment Manual6. Compound A is a clear, colourless liquid with a molecular formula ofC7 H10 . Upon treatment of A with H2 gas in the presence of Pd on carbon,a single product B (C7 H14 ) is obtained. Compound A has a λmax at232 nm in its UV spectrum but will not react with any dienophile in aDiels-Alder fashion. Provide a structure for Compound A, and explainhow you arrived at your decision.7. Identify which of the following compounds is most nucleophilic andwhich is most electrophilic, and provide an explanation for yourdecisions.h4hh4h4 ˜@@44˜ @or4@@˜ @@˜@Organic Chemistry I838. For the following pairs of compounds, explain how the listedspectroscopic method or methods could be used to distinguish betweenthe compounds.a. Use mass spectrometry to distinguish between:OOand2-heptanone3-heptanoneb. Use IR spectroscopy and 1 H NMR spectroscopy to distinguishbetween:OOand2-heptanone84HheptanalChemistry 350 / Assignment Manualc. Use IR spectroscopy and UV spectroscopy to distinguish between:OO4˜ 4 ˜44˜4˜ 4˜˜4˜44˜4and4˜ 4 ˜44 ˜4 ˜ 4˜4˜4ethyl phenyl ketoneethyl 5-cyclohexenyl ketoned. Use IR spectroscopy and UV spectroscopy to distinguish between:4˜ 44˜4˜˜4˜4˜4˜4 ˜o-xyleneOrganic Chemistry I4˜ 44 ˜4and4˜44˜4p-xylene859. In an effort to identify it, an unknown compound, U, was subjected toextensive spectroscopic analysis. Figure TMA2.9a, below, shows the IRspectrum for compound U, and Figure TMA2.9b on page 87 shows the1 H NMR spectrum for compound U. In addition, the mass spectrum ofcompound U was acquired. A molecular ion peak was observed atm/z = 166, and the molecular formula for compound U was therebydetermined to be C9 H10 O3 . A peak at m/z = 121 was by far the mostintense peak in the mass spectrum.Determine the structure of compound U. Be sure to include a concisediscussion of the reasoning you employed to deduce this structure. Aswell, construct tables summarizing the IR and 1 H NMR data, and assignthe peaks in the IR and NMR spectra to the appropriate structuralelements in U. Your discussion should also include an explanation for theappearance of the base peak at m/z = 121 in the mass spectrum.Figure TMA2.9a: IR spectrum for compound U86Chemistry 350 / Assignment ManualFigure TMA2.9b:Organic Chemistry I1 H NMRspectrum for compound U8788Chemistry 350 / Assignment Manual