Ans Exam3 W - A143 Part I. (60 pt) Choose a single best...

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Unformatted text preview: A143 Part I. (60 pt) Choose a single best answer. And 'write that on the cover page. 1. Determine the product. 2; Determine the product; 0 *MH'CJ 00:: so: ace: coo E. a mac 3. Determine the product Na CH C CECCH CH m_____, D. \_/—/ E. None offl'reoboices arecorreot. 4. Which of the following products is (are) formed by ozonolysis of the compOund below? 0/5143 2‘ e {ti-in. a? a? B o o ' c ' <9 L. A“ H—C-Cliz-C—CH3 ' f H—(l'E-CH'z-fi‘ll—H ‘ H3C—é —CH3 @ BothAandBaieformed. E. CompomflsAandCare-fomiedt 5. What is the reagent in the reaction below? CH3 OH CH3 0 0*} OAJ‘W A. 0504 B. 03 c. MCPBA a2Cr207,stO4 E. PCC 6. Rank the following compounds in order of increasing oxidation level (from lowest to highest). 0 0 ' ll - ll A. HgC—C—OH s. CchH3 c. H3C--C-—-H o. Hzc=CH2_ A.A<C<B<D B.B<C<A<D C.D<A<C<B <D<C<A E.D<B<C<A 7. When a compound A with molecular formula C1 2H15 is treated with excess H2 in the presence of Pd, 3 compound having molecular formula C1 2112;, is formed. How many rings and double bonds does compound A possess? A. Compound A has no rings and 5 double bonds. B. Compound A has 1 ring and 4 double bonds. C. Compound A has 2 rings and 3 double bonds. {9 ompound A has 3 rings and 2 double bonds. ' . None of the statements are correct. 8. What type of feature will be observed in the mass spectrum of chlorobenzene? A. An absorption at 3100 cm'1 B No signal at all @A signal at 112 and a signal at 114'ina ratio of3:1 . A signal at 112 andasignal at 114 inaratio of1:l 9. Where in the infrared spectrum can you find stronger bonds? A. Higher molecular weight B. Lower molecular weight C. Lower wavenumbers @figher wavenumbers' 10. Which of the circled C—nds absorbs at the highest wavenumber in the IR spectrum? A. H c. H nomadzo inc—sag wedge H D. H E. H H—cac~@ mc‘éE—E H H 1 1. A compound X shows a molecular ion at 72 in its mass spectrum, and a strong peak at ~1700 cm'1 in flag spectrum. Which structures are possible for compound X? A B. C. o H s 0 2C m Co as g 0 - D. Both oompomds (A) and (a) are possible mm for compound x. E. Compounds (A), (B), and (C) are possible structures for compound X. 12. Which of the following structures is consistent with a compound that displays a molecular ion at 103 and infrared'signals at 2250 and 1600 cm"? on /7 cm 4/ C? H: A} 0/ U ' ' .30 - 3' Q B. C. D. M! a to g 13. What type of signals would you observe in the mass andfor infrared spectrum of the following compound? A». A. A signal at 1600 cm'1 B. A signal at 2200 cm" C. A single mass peak at 92 amu @Two mass peaks at 92 and 94 amu 14. In a typical mass spectrum, a smaller signal is observed at a mass 1 mm higher than the molecular ion peak. Why? A. Due to small impurities in the sample 3. Machine error ( C. IA small percentage of compmmd- having a- carbon- isotope '36 instead of 12C D. Because of fragmentation 15. Examine the IR below and classify the compound. Wm new man mu 2500 29” 1.500 1000 cr- . A. Alcohol B. Alkyne C. Amine D. Acid @etone 16. Which of the labeled hydrogens absorbs furthest downfield in the NMR? Q A. H E i H‘C\ Bl' CH3CH2— C'— Br C=C< CHa—(f-‘CHIBI' ('3’) H H o- H (9 ; HCBr 3 x do fo 1?. Which of the following compounds does not give a singlet in its-NMR spectrum? A. . 2 3, CB) ; CHECCIZOCHS c. ‘sz . I ' _ a} ‘1 Br ' Mac—hemcmcHa CH, CH3 18 Which of the indicated protons would absorb furthest downfield in an NMR spectrum? 0 0 ll . ll II A. CHSCHECOCHa CHSCHZCOCHZCHa c. ClgCHZCOCl-l, l l v T 19. Into how many peaks will the circled proton be split? H “3 H 30 I “‘“CH3 H AS 3.6 ©7 D.8 E. 14 20. Which of the following compounds would give rise to a 13C spectrum with 6 peaks? 2]. Which of the following compounds would not give a singlet in the ]H NMR? one l/W EU) (:05 £17 A ' (9 C D B All of the above F None of the above 22. An unknown compound X has the molecular formula CgHqu. Compound X shows a strong peak in its IR spectrum at 1700 cm". The NMR spectral data of compound X is given below. What is the structure of compound X? 23. An unknown compound X has the molecular formula Cqu 3081'. Compound X shows a strong peak in its IR spectrum at 1700 cm". The NMR spectral data of compound X is given below. What is the structure of com - u und X? _m ms- cuss—I:- A. o 0 C. o >l/u\./\Br W Br/>H‘\( Br D. None of the choices are correct. 24. A student made the following analysis for the 1H NMR of the compound shown below. Indicate which proton is in question, i.e. determine what is x in H3. The inset table provides typical coupling constants. (A) HB He (C) HA (D) none of the above 25—30. Match the 'H NMR spectra shown below with the following compounds. 25. CH3CI-[Br2 3 26. CH3CH2Br b 27, Bl'CHzCHzBI' a 28. CH3CBY2CHzBI' S : 29. BrCI-IZCH2CH2BI F 30. CH3CHBICH23r er A B _ C TMS ms I TMS I____ .H. I_ 5 4 3 2 1 o s 5 4 3 2 1 o 5 s 4 3 2 1 o 5 D E F ms I ms ill. || |_ it |_ H i |__. 5 4 3 2 1 0 a 5 4 3 2 1 o s 5 4 3 2 1 o 5 G none ofthe above 2 {1? am!“ Part 11(26 pt) F iii in the boxes with organic compound or reagenfls). LNaNHZ Nam—12 1. H—CEC-H —2——--—----——-i-- H30HZC—CEC-H —>— \ M1, aims RCO3H H30H20 H ,4————— H— H CH3 . l ' I Gm KMnO4 - mCPBA —i. ' \ 1.03 . 2. CH3SCI-I3 1. 0504 m—" 2- NaHSO3, H20 Cr03 H30+ n O (“X K 1. 0 _3_.. H 2. CH3SCH3 E :c i o o _. fl 6 ’ {3 CW3 C 3 l CH3Br HSCHQC—w CEC-CHg. (only product) Part III. 1'. (8 pt) Determine the structure at the compound CgHmO; cam»: mmgfions 171cm“ ...
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This note was uploaded on 10/06/2011 for the course CEM 251 taught by Professor Rathke during the Spring '07 term at Michigan State University.

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Ans Exam3 W - A143 Part I. (60 pt) Choose a single best...

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