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CHEM 2212Exam1 key

CHEM 2212Exam1 key - NAME ID first CHEMISTRY 2212 EXAM 1...

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Unformatted text preview: NAME ID# first CHEMISTRY 2212 EXAM 1 January 30, 2008 Be sure to read each question carefully. This test must be taken in pen. Tests taken in SCORE pencil will not be graded. Partial credit will be assigned where appropriate. To receive full credit you must answer each question completely. Relax and good luck!! 1. (8 pts) Draw the fragments (charged and uncharged) resulting from the McLafferty Rearrangement(s) of the following compound: -+ 2. (8 pts) Provide all of the possible alpha cleavage fragments (charged and uncharged} for the following compound: Min—WM /& ” OH 10. MN} Total: CH3 l ch/ %\ 5H ; ‘4 Z 04;” 1‘th 1 3. (12 pts) Complete the following reaction schemes by providing the appropriate elimination product or products. Make sure to indicate the proper stereochemistry when necessary. Clearly indicate the specific type of elimination reaction in the boxes provided to the right of each reaction scheme: Indicate Reaction Type (E1, E2, E1CB) | (96) Hac—e—o Na CH3 Strong Hindered Base ———> DMSO CHgCH3 TosO/,, CH3 OTos (9 9 H300. “\CHs 0.01M Na OCH2CH3 ——————> 80% aq EtOH, 160° C CH3 Concentrated Na GGOCI-lzCHg E DMSO H 2, .IIO I 1.) Br 0 OH NaOH —> EtOH E/ E unnecessa- 4. (10 pts) For each of the structures provided below, indicate the total number of chemically/magnetically distinct proton types. ”bawawH @930“) 5. (10 pts) Compound X, C11H14O, produces the 1H NMR spectra shown below. Propose a structure that is consistent with the provided spectrum. In addition, you must assign/identify each of the peaks in the NMR spectrum. You must be very specific with your labeling in order to receive credit. Simply labeling a peak as a “CH2” group is not acceptable. You must clearly show which specific hydrogen(s) in your structure correspond to which peaks. Important IR Data: There is a strong absorption detected between 1670-1780 cm" Compound X: arDMAM H‘§ : A Doublet. 3H C, Triplet. 3H 6 a A Quartet, 2H Complex Multiplet. 5“ b Ouartet, 1 H 6. (10 pts) An unknown compound contains C, H, and 0. Its mass spectrum and IR spectrum are shown below. Use the provided spectra to deduce a possible structure for this compound and draw the structure in the box provided. In addition, provide the molecular formula in the appropriate box below: Molecular Formula: CsHtO—L Mass Spectrum: 100 Structure: HS-NU-UDZ? 80 C) O Relative Intensity A O 20 10 15 20 25 30 35 40 45 50 55 60 65 70 75 IR Spectrum: [DD 01 U IMINDI'ILI lllflLtlifil 41100 3000 200“ liflfl 1000 5ND IlFWENUI‘II ERI ~II 7. (10 pts) The 1H NMR and IR spectra of a compound with molecular formula C6H120 are shown below. On the 1H NMR spectrum, the splitting of each peak is magnified for clarity, and a line listing of the peaks is presented in the upper left hand corner, listing the splitting and integration of each peak. Draw the structure of this compound in the box provided. Structure: triplet, 3H doublet, 6H quartet, 2H septet, 1H [00 TR INS” [TTINt E l ‘4' 01 I: “100 3000 200i ”"0 1000 “0 IRVENUHI if" -I I 8. (11 pts) For each of the following sets of compounds, circle ALL of the bond(s) that could be used to distinguish between the compounds in their IR spectra. Note: You may circle bond(s) in both compounds, or only in one of the two compounds, depending on how many distinctive bonds exist. (a) o 0 II II H3C—C—O—CH3 and H3C—C—. (b) H2 @C—C --CH3 and HgC—CZC—CH3 (c) H Hsc—c2 CH3 and mow—CH3 (d) CH3 and CH3 (e) \N (.3 9. (11 pts) Use the following spectra to determine both the molecular formula and the structure of a “mystery” compound that contains C, H, and O. In addition, provide the structure of the charged molecular fragment that has a m/z ratio of 45. The fragment must be drawn in the blank space on the mass spectrum. [Hint hydrogens attached to atoms such as nitrogen and oxygen do not cause spin-spin splitting on a 1H NMR spectrum] Molecular Formula: CH Hmo Structure: DH Mass Spectrum: M+ peak = 74 m/z 100 flS-NU— 0933 80 >3 r: 2 q; 60 4.1 g Q) .2 _._I _O 40 Q) o: 20 o IR Spectrum: lDD TIHNSHITTRNCEI '4! UI I: I IJDO 3000 200" 1 5 DO 1000 5 [IO HRVENUHI ER! -|I 1H NMR Spectrum: Doublet 3H . ’ +np\<,‘\’ O“ 0‘ e— m. 3H b b VA\ A Complex multiplet Complex multiple! Iesembling a quintet. 2H resembling a $extet, 1H Broad Singlet, 1H 9\ PPM 10. (10 pts) Compound Y, CsH1602, produces the 1H NMR spectra shown below. Propose a structure that is consistent with the provided spectrum. In addition, you must assign/identify each of the peaks in the NMR spectrum. You must be very specific with your labeling in order to receive credit. Simply labeling a peak as a “CH2” group is not acceptable. You must clearly show which specific hydrogen(s) in your structure correspond to which peaks. Important IR Data: There is a strong absorption detected between 1670-1780 cm" Compound Y: Singlet. 9" C 0\ b Doublet, 6H Septet, 1H PPM ...
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