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organic II exam 1 key - «H 4:122 Exam 1 page 1 of5 with Y...

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Unformatted text preview: «H? 4:122 Exam 1 (2/20/08) page 1 of5 with Y = yes, N = no, or ? = maybe. Use the ? w [3 pts each structure] Name ! E f 1) For each structure indicate whether you would expect a peak in the indicated area by filling the box you don’t have enough information to be sure. {053$— structure -) vaeaks observed Jr C5H14O O | | ‘COEH O-H, N-H stretch CSp—H stretch Cspz-H stretch CN : COgH CI C5p3-H stretch triple bond stretch C=O stretch M3 M u 7 u N 424%22 «'42sz J— _;Z_ N Y 2) For each structure, fill the box with the requested number or word. [3 structure number of p-orbitals g number of pi electrons «{— aromatic, antiaromatic, neither ”Vi/WHEEL CHOT (MOW/w q. : 2 NEW (0 HUN/mm a team t Cnfli’fij r0 pts each structure 417' A 3) Draw the product(s) of the reactions, indicating stereochemistry when appropriate. No mechanisms, just products. [6 pts each] 4:122 Exam 1 (2/20/08) page 2 of 5 Name (A 6N “~ —» at: [on + “x [w \/\ 7’ 3 \752/3 7 {J (1 equiv) & 'D [)V 4) Draw a set of resonance structures, each separated by the double headed resonance arrow. Then draw a representation ofthe resonance hybrid. Circle the latter structure and label it ”hybrid” [8 pts] W ..__.. //\®/§/ W /%/§/ ® /7/ Mgwfi‘, 0R Sa— $5? 5+ WSW _M‘__/._v /0 4:122 Exam 1 (2/20/08) page 3 of5 Name l E”) I 5) For each type of magnetically unique proton in each structure, provide the number of protons and the expected multiplicity. Use as many boxes as appropriate. if you identify more unique protons, write the info into the box next to the structure. Use the whole words singlet, doublet, triplet, quartet, quintet, sextet and septet where appropriate. For multiple couplings, be specifi '.e., doublet of doublet but don’t use multiplet) [20 ets] fl Bil/W \t’l l4!» 1‘lBr CI —\ I CI: H :1“ ...... i at. ,_t Br l7 . Ha (number) (1, 3 Q g Ha (multiplicity) Do (ELEV , fiinéLZT mew? ézuéLgf‘ WT— 7/ L( Hb (multiplicity) Uppgfl?fgr g wag“ QUW‘E‘V Hc (number) 7/ g 3 Hc (multiplicity) POUSSKE)‘ slpéwr ’ Hd (number) i W éwéua'r He (number) He (multiplicity) / + W Wm 6) List the three compounds in increasing order of acidity of the indicated protons. Place the letters in the proper order below. [4 pts] H H H H H H order: L<L<L W5?“ Q g 2? Reasons: I . 7 7 -. 7 ZD Wfifmilsfl l . (a W PM 63 c3 :7 W 1" [I ' D 4:122 Exam 1 (2/20/08) page 4 of 5 Name lL’EL/ Amswal Us?) coma/"r 2H 3 60122331sz #2 W 7) Read each statement carefully. On the line at the beginning of each statement, indicate whether the statement is true or false by using a capital T or F. If the statement is false, circle the words or short phrases that make it incorrect and write replacements that would make the statement true. Example) _F_ Lecture for this class meets MWF 3% €’%0 AM '5 a) ? The opioid pain receptor senses a substrate via structural features that include hydrogen bonding (OH), a benzene ring dr phili nteraction), and an ion (ammonium N+). 3 b) ’E: Retinal has several alkenesflconjugated with an aldehyde, attaches to a protein in the retina, is supplied to the body as [email protected]), and triggers the vision process via a Xlal 9 equatorial M l c) l MRI is a diagnostic medical technique that uses NMR signal from NMR-active atoms within tissues; it often involves the use of a metal—containing contrast agent. / d) l As the length of a polyene increases, it is capable of absorbing light at a lower energy as the gap between the highest energy occupied orbital and lowest energy (empty) antibonding orbital decreases. or supplements the role ofthe atmosphere that absorbs “gm. < 6 ' U 3 f) F Mass spectrometry works by generating a radical cation (i.e., the molecule less one electron); the observed peaks are due to the molecular ion or to thgagments of the molecular ion. l 3 e) P A sunblock absorbs UV light that might otherwise cause sunburn or suntan; in part, it replaces / 3 g) ( Spin-spin splitting occurs between adjacent types of magnetically-unequivalent protons (i.e., ll @onds or fewer) and follows the ”n+1" rule for observed peaks (due to n equivalent protons). D _ Cl 4:122 Exam 1 (2/20/08) page 5 of 5 8) All ofthe data represent a single structure. In the box to the right of each type provide the information that you concluded. Don’t list the data again—give some interpretation. [15 pts.] Mass spec (m/z peak, intensity) 27, 15 39, 70 42, 16 29, 12 40, 12 69, 47 38, 11 41, 100 70, 95 71, 5 Infrared 4000 3000 20E|0 1500 cm" (Formulas, fragments) M's-C710 772') C; Hi0 mam Lures owl 4i sts new m7) Name f ( (Peaks and functional groups) H-NMR d (J: 7.8 HZ) q ofd(J=15.5. 6.8) d ofd (J: 7.8.15.5) / d(J=6.8HZ) \ ppm l’l" 'l'l'l'l'l‘ll Z (0461 .J‘ H (WED/“ME (shift, multiplthy, # hydrogens, partial structure) 49 13C—NMR (chemical shift of peak) (shift, funcggnal group) J' 'D 1) 194 ppm ieLL’r 3‘0 péfilfi’a) 2) 154 ppm (,C—O RU" 3) 135 ppm \IS—Zkl 5g 4) 19 ppm \q (25??) Overall structure Eff—”W JUSW' ( E {M “Viol/LY, ) (R 4,?) u “ ' MWW \":_. /\ll— / \lé» + ( Oak; W“ 9 M5 W ...
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