30B_Winter06_Exam1_Key - Organic Chemistry 30B Winter 2006...

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Unformatted text preview: Organic Chemistry 30B Winter 2006 EXAM 1, Page 1 1. THEORY 1. a) (12 points) Give the number of expected signals (ignore splittings) in the 1H and 13C NMR spectra of the following compounds: CI OH 6H3 1H NMR: 3 13C NMR: 3 b) (18 points) Sketch the 1H NMR spectrum for the compound below. Be sure to consider chemical shifts, coupling patterns, and rough relative intensities between each spin system when drawing your spectrum. Please label H’s on the structure (a,b,c, etc) and corresponding peaks: 0 t W b Is. 10 9 8 7 6 5 4 3 2 1 0 Organic Chemistry 30B Winter 2006 EXAM 1, Page 2 7 Name II. SPECTROSCOPY two lines only in the l3C—NMR spectrum, in the absorption bands on the spectrum and provide its ' (Assign peaks on or below the spectrum) u @ZL. Z :f/ compound C6H603 ")0 "WIVTKEI '4' “00 3000 200i ISM £000 5” “Hm”! «I Name Organic Chemistry 30B Winter 2006 K EXAM 1, Page 3 fi/ 3. ( 15 oints) ' ecular formula C4H402 has the following 13C NMR spectrum. Its 13C NMR spectrum: Organic Chemistry 30B Winter 2006 I EXAM 1, Page 4 ‘ ' Name 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: 3 Degree of Unsaturation: (Please assign all recognizable peaks, 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 (CCl4): m "MIYMEHII Organic Chemistry 30B Winter 2006 EXAM 1, Page 5 Name 1H NMR spectrum for question 4. Please assign specifically what peak is what part of the structure (by letters or arrows; show structure again on this page): 2M; ° (4 Organic Chemistry 30B Winter 2006 EXAM 1, Page 6 %’ Name 13C NMR spectrum for question 4. please also assign the 13C signals to carbons of structure, except for those purely aliphatic or aromatic; show on this page: ...
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