chem372w08hw3 - Chem 372 Winter 2008 Homework Assignment 3...

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Unformatted text preview: Chem 372 Winter 2008 Homework Assignment # 3 Due at class Tuesday 29th Keep a copy of your answers for comparison to the answer key since you will not get the corrected assignment back in time to review it before the test on Thursday 31“. 1. The spectrum below is for a sample inadequately labeled “Butanol”. There are four possible isomers of C4H90H. Write down the four structures and on the basis of the spectrum decide which one it is. Make sure you clearly explain why the other structures are not acceptable and assign each signal to the appropriate H in your structure. 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 PPM 2. Compound X has the molecular formula, IR spectrum and 13 C NIVIR spectrum shown below. Use this data to arrive at a structure for X. Make sure that your reasoning is fully and clearly explained. 100 :1 mm' 10.0011 00-1 11 8 metal) 5.522 2953.00 0.475 1452.00 10.255 1351.00 20.742 1114.00 «3.55: 105.00 3.955 550.00 43.240 903.00 55.775 534.00 54.935 332g C6H14O \ /CH2 - CH3 \ CH2 / \ — CH / 200 180 160 140 120 100 BO 60 4O 20 O 3. Compound Z has the molecular formula C7HJOO3 and the IR and 1H NMR spectra below. Use this information to arrive at a structure for Z. Make sure that your decision is fully justified by a clearly presented analysis of the data. / Jg'zv IR Spectrum (KBr disc) 4000 3000 2000 1600 1200 800 V (cm'1 ) 1H NMR Spectrum (400 MHz, CDCI3 solution) expansion expansion —I—I’—‘_ 2.8 1!- Compound U has the molecular formula C6H1004 and the IR, lH andHC NMR spectra shown below. Interpret them as fully as possible and arrive at a structure for compound U. M20 IR Spectrum (liquid film) 4000 3000 2000 1600 1200 800 v (cm’1 ) 13C NMR Spectrum (500 MHz. CDCI3 solution) DEPT CM CM CHl proton decoupled 200 160 120 80 4O 0 5 (ppm) 1H NMR Spectrum (200 MHZ. CDCI3 solution) expansions ...
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