First exam herriot - CHM 2211 ORGANIC CHEMISTRY II First...

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Unformatted text preview: CHM 2211: ORGANIC CHEMISTRY II First Exam, Form 1 Section 02, "Professor A. Herriott February 5, 2008 No electronic deviCes (calculators, cell phones, laptops, etc) may be used or consulted during the exam. All scrap work should be done on the extra page provided; no additional paper may be used. Your name and Panther II) should be placed at the end of this paragraph to indicate acceptance of all policies and on your answer sheet. Be sure to include the form of your exam on the answer sheet. Name Panther [D Part A (51 points, 3 each): Enter on answer sheet with number 2 pencil 1. The mass spectra of alkyl bromides and chlorides are characterized by an unusually intense . A) base peak M". +2 peak B) parent peak ) None of these C) NT. +1 peak 2. The IR spectrum of which type of compound will show a strong broad band at 3500- 32000111‘1 ? - A) Aldehyde @Carboxylic acid C) Alkene D) Ester E) Ketone 3. When nucleophilic addition to a carbonyl group Occurs, the carbon attacked undergoes ' hybridization change: A) 3132 i Sp3 D) $133 5132 B) sp —eee+ sp2 E) Sp2 —~m——> sp C) sp ——*———+ Sp3 4. Which compound would have an UV absorption band at longest wavelength? CHZCHCHZCHZ CHZCHCHZCHQ CHZCHCH= CH2 [email protected] an em (:HchonzcrH2 CH:CHCH=CH2 d c: IV V 1 B)II (3)111 mw my Page 1 5. Which of these dienes can undergo the Diels-Alder reaction? A __ 1,2-Heptadiene D) 1,5-Heptadiene E) 1,3-Heptadiene E) 1,6-Heptadiene C) 1,4—Heptadiene 6. Which of the reagents listed below would serve as the basis for a simple chemical test to distinguish between (CH3)3COH and (CH3)2CHCH20H ? A) NaH B) NaOH/Hzo C) Brg in con D) Litmus paper (E? Cr03 in Iazso‘1 7. How many 13C signals would 1,4—dimethylbenzene give? o A)1B)[email protected] D)4 E)5 8. Which compound would have the shortest carbon-carbon single bond? A) CH3-CH3 D) CH2=CH—‘CECH B CH2=CH—CH3 E) CH2=CH—CH=CH2 HCEC—CECH 9. A compound with the molecular formula CmHM gave the following 1H M spectrum: doublet, 6 1.2 singlet, 6 2.3 septet, 6 2.8 multiplet, 5 7.1 A possible structure for the compound is: IV V A)[email protected] (3)111 33)“? E)V 10. A reaction under kinetic (or rate) control will yield predorninantly: A) the most stable product. BE the product that can be formed in the fewest steps- ) the product whose formation requires the smallest free energy of activation. the product with the greatest potential energy. E) the product with the least potential energy. Page 2 1 1. What is the principal product(s) formed when 1 mol of methylmagnesium iodide reacts with 1 mol of p—hydroxyacetophenone ? o «£32K CH3MgI A HO 0 0* m 0* IMgO + CH4 Ho ‘0 IV V B) II C) 111 D) IV E) V 12. What product(s) isfare formed in the following reaction? 0 LiAID4 D20 H —w—» ——+ :2 CchHZCHchCHZCH3 ether CHgCHZCHgCI-IZOD + CH3CH30D @ CHgCHgCHgCDgOD + CH3CH20D ' ) CH3CH2CH2€D20H + CH3CH20H D) CH3CH2CH2CHDOD + CH3CH20D E) on I CH3%ch$330014ch3 13. 0f the spectrometric methods discussed in this course, which one does not involve absorption of electromagnetic radiation to induce a transition from a lower to a higher energy state? A) Nuclear Magnetic Resonance __ -,. Visible Spectroscopy B) Infrared Spectroscopy w Mass spectrometry C) Ultraviolet spectroscopy Page 3 '14. What is the product of the following reaction? @4ch2 o o + II ll —r- ? CHgC—CEC—CCHE, COCH3 : : “COCHg : : ‘COCH3 : : :COCH3 COCH3 COCH3 I II III COCH3 @COCHa com-:3 .1 B) II C) III D) IV E) V 15. Which reaction is an oxidation? A) RCHO —————> RCOZH D Two of these B) RCHZOH —e~—-—~> RCHO All of these C) RCHZOH ———> RC02H 16. Excluding splitting, how man}r 1H 'NMR signals would the following compound give? CICH2?HCH3 17. What product(s) would you expect fiom the following substitution reaction of 14C- labeled propene? N—bromosuccinimide 14CH2=CH-—CH3 —.___H__,.. ? ROOR, CC14 i4CI-Iz=CH—CHgBr alone i. _ 14CH2=CH~CHgBr and CH2=CH——”CH2Br in equal amounts CH2=CH—14CH2Br alone D) More ”CHfCHCHzBr but a little CH2=CH~MCH2B1~ B) More CH2=CH14CHgBr but a little MCHfCHCHgBr Page 4 cf *1! Section B: @oints, Xeach) Give the principal organic product of the following reactions, indica 'ng stereochemistry where applicable: 0 ll M _____,, / a) 0% + A/ SET SA 2. H20, NH4C1 b) NaBH 4 —-—-—-—-—P— / o 1120 . 0) ED CHZOH d) PCC, cuzm2 flaw: (PPC = </ \NH“Ci + Croacr) \ NBS, UV light 3 8 ( WE :m) C O Section C: (15 points, 5 each) 1. Using reagents of 4 carbons or less, what Grignard reagent and what carbonyl compound would you select to produce 2,4-dimethyI-3-pentanol. N3 + )Mafl” 2. What two compounds would you choose for a Diels—Alder reaction to prepare the cyclohexene diketone shown: a O 3. How would you convert cyclohexene into the ketone cyclohexanone in two steps? Section D (12 points, 6 each) 1. Sketch the proton mnr spectmm you would expect fi'om ethyl acetoacetate, whose ' structure is shown: Identify the number of signals, the splitting of each signal, and the approximate position for each. How many signals would be observed in the carbon-l3 nmr spectrum? 2. Interpret the information given and assign a structure to Unknown compound B. B shows a molecular formula CsHmO from the mass spectrum. The infrared spectrum and proton nmr are given on the following page. (The inserts are the expansion of the adjacent nmr signals.) C-l3 nrnr indicates 4 signals closely spaced in the aromatic region around 125 ppm along with two other signals, at approximately 40 and 60 ppm. Bonus question (2 points): Name any chemist who won a Nobel Prize, the approximate year, and the discovery for which the award was given. ...
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