30B_Spring06_Midt1_Key - Organic Chemistry 303 Spring 2006...

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Unformatted text preview: Organic Chemistry 303 Spring 2006 . , fl EXAM 1, Page 1 ’ ' Name I. THEORY 1. a) (12 points) Give the number ofe expected signals (ignore splittings) in the 1H and 13C NMR spectra of the following compounds: \ H I!” H 09114er @H \ $1??? K H \ w Wlfialle?’ ff(:r3>H ‘ Z “0‘4 13C NMR: 2- 5,5 5 7/ a% b) (18 points) Sketch the 1H NMR spectrum for the compound below. Be sure to consider chemical shifts, coupling patterns, and relative intensities between each spin system when drawing your spectrum. Please label H’s on the structure (a,b,c, etc) and corresponding peaks: ~77 Organic Chemistry 30B Spring 2006 EXAM 1, Page2 , . W g 3/ Name 11. SPECTROSCOPY 2. (15 points) A compound with molecular formula C3H40 has the following IR spectrum. It shows three lines only in the 13C-NMR spectrum. Assign recognizable IR-absorption bands on the spectrum and provide its structure in the box below: Degree of Unsaturation: Z (3x2) +3 ”V : Z Z Etc '2, @ (Assign peaks on or below the spectrum) 100 "WHITTWEHI +1 “mm a. O C— 0 Q) Organic Chemistry 30B Spring 2006 .. EXAM 1, Page 3 , Name 3. (15 points) A compound with molecular formula C6H9N has the following 13C NMR spectrum. From this information only, deduce its structure and assign recognizable absorptions in the 13C N MR spectrum. You MUST provide all the relevant information (peak assignment) to get maximum credit: 3 Degree of Unsaturation: (éxz)+2, -? +/ Du: Compound CngN 13C NMR spectrum: Name Organic Chemistry 30B Spring 2006 EXAM 1, Page 4 ,, y 4. (40 points) A compound has the molecular formula C7H1002. Deduce its structure from the IR, 1H NMR, and 13C NMR spectra given below. You MUST provide all the relevant information (peak assignments) to get maximum credit. Draw the structure in the box provided: Degree of Unsaturation: } (7 Ya) +2 - l0 Wt: Compound C7H1(,O2 (Please assign all recognizable peaks in all spectra, including indication of coupling type and relative intensities in 1H NMR, chemical shift-related assignments for both 1H and 13C NMR, and typical IR stretch frequencies) IR (liquid): [DD “WITTIKEIXI Organic Chemistry 30B Spring 2006 @: E EXAM 1, Page 5 Name 1H NMR: Assign specifically what peak is what part of the structure in addition to assigning integrations and multiplicities (by letters or arrows; show structure again on this page): 1: @ a M K) kw \ q. ._..__ K) g \ ,_ a“ \ w/fi 0‘5 I O i i 5 Q ”‘U V\ i K) N K) 4‘ 4: i x 5 I: 3‘ \ / 0 PPM Organic Chemistry 303 Spring 2006 ' EXAM 1, Page 6 ' 3 Name 13C NMR spectrum for question 4. Also assign the 1"C signals to the structure, except for those purely aliphatic; show on this page: ...
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