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    Exam 2 1995 KEY PDF

    Загружено:

    aegais

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    © All Rights Reserved
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    Отметить как неприемлемый контент
    из 8
    SECOND EXAMINATION 7:30 pm, NOVEMBER 7th, 1995 Duration: 2 hr Name. Lab TA., Gif you do not know his/her name, give time of lab section) This is an “open book" examination; you may use anything which is not alive. Score: Va v. 0 total: /100 There are 9 pages in this exam; please check now to be sure you have a complete set. Page 9 contains spectral data for problem III; you may tip it out for convenience. Be sure the remaining pages are well stapled when you turn in the exam. Please be aware that a small number of students will be taking the exam at different times up until the afternoon on Wednesday. It would be well not to discuss the exam until after that time. Pledge: I. Consider the structure of compound A. ea t How J cH4 I ZL Nn a A Qa a 6 : cl A. (8 pts) b 1. Place a circle around each group of equivalent H and label them a,b,c... 2. Draw your best representation of the proton NMR spectrum on the chart below, assuming a simple first order spectrum at 60 Miz. Take care to show your calculations for arriving at the chemical ‘shift positions for groups of equivalent protons. Show the multiplicities (pattern) and specify approximate coupling constants, where relevant, in Hz, ti Hii Tee TE TAL TM TAH UR a TT FE SG = OBTAOANB= LOE C115 ow "new Aart”) 8H dovblot, 127 ES 1504 105 259 C250 on wu hart) 1 satel, Je7 G22 b20F bor tas3 = 2.7% C.3t) 24, trplet, Jom Gye (20 t2.20 $0.3 = 3.3/ ¢3%0) 2H, Prple I°7 B.(4 pts) Predict where peaks will appear in the region 4000-1500 cm! in the IR spectrum, and their approximate relative intensities (weak, medium, strong). Q-H stretch — 2990-235 eur! CneSiusn or strong) Many <-h C20 stretch — 1730-)700 gz! strong. € (4 pts) On the chart below, draw your best representation of the parent ion region in the mass spectrum. Label the axes and take care to show approximately correct relative height. You may also stipulate the relative heights as percent of the highest, Pea or in terms of peak height ratios. ee yp! na\, Ni SS 133 39336 Ngy D. (4 pis) Imagine the UV spectrum for A. + a. How many peaks would be observed in the usual spectrum, from 200-400 nm? . Would the peak of longest wavelength be between: 200-250 nm (circle best answer) ¢.Would that peak be Gow retun, or high intensity (magnitude of )? Explain. mart 2 por averinp E.(5 pts). 1. many peaks would you expect in the C-13 NMR Spectrum? Explain. Chy groups Ar Should give Z peaks He cyano (CN) <— ptgyhe => Met quite comet Maize. : benaeeritt <— wo peak in) 2100 -Joco rego), 1300" KkS0 Kron) TIL Consider the spectral data for molecule B (ast page of the exam; you may tear it off) alkenes (consider each case separately) Hee R HJR Ree \ R ? 0 iH v R a. \ rr aed 380- Jo20 , h20~/ét0 alkynes: H is . B. (4 pts). From the mass spectral data, what is the molecular weight of the compound? Give an estimate of the number of carbon atoms. Bef, ee What common elements are ruled out by the mass spec data alone (cross out your choices): HEN? Oe rt cr of he ) 4 too heavy: C. (4 pts). From the UV data alone, which of the following functional groups are ruled out? Cross ‘out Your choices and explain in a few words. \ v Z me RZ R= RCEN: No Howe long a poate ? M>T* shoul Show. D. (3 pts) oe carbon atoms are indicated in the C-13 spectrum? E. (6 pts) For each set of equivalent protons, give the IH NMR chemical shift, the relative area, and describe the splitting pattern including approximate coupling constants. @® § vos Ct J*7, 34) () 5 1% Gpintt, I= 2,24) Os 236 Cs, Id) @ triplets 77 Cif, Nort to cad 9 gatd, Je7 cH next to Cts -oy fast exchange, 5 Alkywe lower emetay compared te CN. 1. Draw the structure for E which best fits the data given. f & Hy hy wy 2. Explain carefully how your structure E is consistent with the pattern in the NMR spectrum, including chemical shift, peak separations, and relative areas. LCs me splt by DD nplet of egonl height at 609, fu. ch aH | & ow a appeals at <0 5 Sarglet Cue HW on nYjncedt Cc)” Might hale seow Seen! Long rapize coupling; Met FEN. = SOS; wot much zpliting=> we pdhpaceat C-H 3. Explain how your structure is consistent with the IR data. JR shows C-¥ stretch xt 3080, 2700 cw"! ae stretch ut 430 eur! 4. Write the structure for anion C, and explain how it reacts with D-Cl to give rise to isomers D and E, ds ob Cy fly = 7 se =< CH 3

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