Summer 2007 test 1 - (Mam 228 Test I W5: / Dr. Wells Summer...

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Unformatted text preview: (Mam 228 Test I W5: / Dr. Wells Summer [I 2007. score = Opscan * 75/15 + essay = fi * 75/15 + "i = [00 WO‘J' . [f/ Essay A. Draw the block diagram of the NMR Spectrometer (5 points ) l6 tel 15 Sg’lnt 539°“ Tl)“ 55"”? use/J. o A (at: H" (9 4”“ Essay B. On the next page: (10 points) A V y o Discuss key features ofthe IR Spectrum. - Draw the predicted 1H NMR spectrum . - Label the different types ofprotons (i. e. chemically equivalent) in the compound with letters (a, b, c, , r l) — Indicate which protons are responsible for each resonance (by letter). - Draw the resonance at the correct (estimated) chemical shift (6) - Draw the correct splitting pattern for each resonance (ire. doublet, triplet, quartet . . . ) - indicate integration with relative numbers of protons above each resonance. (ie. 1H, 2H, 3H . . .) - Draw the predicted 13C NMR Spectrum. - Label the different types ofcarbons (i. e. chemically equivalent) in the compound with letters (A, B, C,. . .) - Indicate which carbons are responsible for each resonance (by letter). - Draw the resonance at the correct (estimated) chemical shift (5) - Include the DEPT information above each peak (i e. C, CH, Cl-Iz, CH3) 5 ojfcuA a\\'yw55f\v\ I 0 Discuss IR: '_ . A CHM {1"0 O 5 (ppm M ’50 Essay C. Some random stuff. (10 points total) Draw a compound with molecular formula ofC4I-le that has only two singlets in the 1H NMR (3 points) Draw a compound with molecular formula ofC3H,3 that has only 3 lines (peaks) in the '3C NMR. (3 points) \ . l r / thhfir LM— C_—-—- (“<54 / l l H M 3c M ""1 L 15 There. mf‘jk’} be all“! Cot/J (“Afimfl‘ Draw the final product of the reaction sequence below. (4 points) 1) KMnO4, OH", heat 0 1) OH"? 2)}130+ K 3)].JAIH4 ’ 4)H3O+ O ___, 0 Lo 4 3’} 42 l) 1 0 ’L A l Q\€;~V"‘)L > q) t A 5 3) 47 “4) :. W/‘LWH/ Q 0Y\ 1 . Reaction ofcis-2—butene with cold dilute KMno4 yields __ L/Fg ' ® a meso compound 5 7 "\ V“? A”‘* + Ll i,“ grimy} B. araeemie mixture 0'“) w Vi C. an aldehyde \ . H Dl’l ! D. a ketone e—D \ J i E. a primary amine W yo I /\ M Lilo 0% CH / 71.” H “l 2. What is the most likely product ofthe reaction below? 3 l) Hg(OAe)2 Viv-{KN m )9“ 2) NaBH4. OH" 9 —_—> . e c K OH O OH HO O OH 3. The word “photo” is dropped from spectrophotometer to name the NMR instrument because _ A. photographs ofthe sample are no longer required with Fourier Transform techniques Q3) lenses and mirrors are not used in NMR instruments (3. liquid helium would freeze light D. the strong magnets don‘t allow light to pass through the sample E. light interferes with magnetic resonance l5 4. Peaks in an infrared spectrum are generated when ' A. ionic bonds are broken B. covalent bonds are broken C. the nucleus splits D. electrons are promoted to higher energy orbitals (ET) atomic movements resonate é; 5. TMS is used in spectroscopy because A. is does not absorb IR wavelengths B. it does not absorb in the fingerprint region C. it is cold enough to induce superconductivity ® its signals are upfield of most organic peaks E. it dissolves most common Organic compounds 6. What is the most likely product of the reaction below? " f, \/ \ri Merl/e“ “mi-“O tiriLinisri3 go “ 2) H202. OH‘ 9 —_—> . i\>§ OH @K c K OH 0 iv \rmtl" 7. FT NMR instruments are filled with liquid helium so that _. A. the magnetic will float n {3HJ . ,- i . r“ the electromagnet wll superconduct (V i f \ /M i . the sample will not overheat fig) Cd/ ii“ I) the sample will remain in the solid state \ E, extra neutrons are absorbed M i /0 Lil C/ 5 C it / \ M 8. The Markovnikov rule is based on . / " 5 A. the amount of water present (if “H //"l5,.;> B. stability of alkene Ctr-t5 5;“ M an ’ L lg , ht” t C steric crowding directs nucleophile to less crowded region \C A") O” l' ‘i i "l ‘ " ixu ' CF13 5- U / D p anal intermediates yie d iacennt m t res I + \\ big} I 69 formatiOn ofthe most stable carbocation k I! f/ CQOM («mks try] C. 1) . t4 Inuit? CH3/ a 03/} 9. Reaction ofcis-Q-butene with a peroxy acid followed by aqueous sodium hydroxide yields Ar 21 meso compound @a racemic mixture C. an aldehyde (g D a ketone E. a primary amine / a mam . Inspect the reaction sequence below for questions 10 - 12 Q) (’9 >i3r __,Mgm x i: ’ ' H? 0"” other /\ Crfljhw W WJR 1o. x=£ A We Eddie is doing stuff in the lab . . . 1 3. Eddie added aqueous chromic acid to an unknown, but pure, organic liquid. The color changed from orange to green. This indicates that the unknown could be . 0 V .. 0 V i/ . X l. 1 alcohol ll. 2 alcohol Ill. aldehyde Iv. ketone @iiiiiiii Cr“ -—-—+> Cr“ root“ B. i’ ii, iv (Liz-fl VJ“) (wian I c. i, iii, iv 0W“??- 9 E— l} D. ii, iii, iv E. i, ii, iii, iv O'r‘jnhiL w‘") affix In a separate experiment, and several days later, Eddie added aqueous basic potassium permanganate to hexanol and heated for 10 minutes. A thick brown precipitate formed. Eddie collected the browu precipitate in a Buchner funnel. He acidified the filtrate and noted an oily liquid floating on the solution. 1 4. The brown solid is . O 0W 0 ll E) m u we n0 - A. hexadexyl tartrate 0 “‘3 N 58’ Li?) A B. boron hydride W + M “461% A (54-) by“ b C. diborane \ if *"' ® manganese dioxide V \4 aluminum hydride 0 Wk .4 ii 0 1 5. The IR spectrum ofthe 0in liquid is . /\ I (X) ...
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This note was uploaded on 06/19/2008 for the course CHEM 228 taught by Professor Jung during the Summer '08 term at Campbell University .

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Summer 2007 test 1 - (Mam 228 Test I W5: / Dr. Wells Summer...

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