Summer 2001 test 3 - Chem 228 SSII 2001 Test 3 Dr. Wells...

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Unformatted text preview: Chem 228 SSII 2001 Test 3 Dr. Wells Grade = opscan“ x 4 + quizamalam = L) x 4 + (0 Questions 1 - 8 concern the reaction of substrate X with the reactants shown. No”! R CHS/KH OH 200 c H2N— NH2 ———> 2 CH H H IBI/ 3 131/ CH3— ?—H C C CH3/ \H CH3/ \H H CH3/ A B D C HCN 3 CH/ \H 3. 3 ; 3 would most likely be ll ll 1 II E, Xe“ CH3— C—H C CH3— C—H CH3— C—H I -"' '- I / \ I III II'.II (i CH3 H | '11} B c D ; 4 would most likely be 0 O 0 / \ / \ 0 H H3C E H g h) 0 C / H / \ / \ 0 H c \ / C C/ H3C O H 3 O HBC/ \O/ A B C D 10% NaOH —> 5. ; 5 would most likely be. 0 O OH H 0 II n | | u H3C— =c— c\ h) H o ’C___ C: H3C— c— c— c\ I l H | || H3C | l H H H . H C ,C— C— C\ \ H H 3 | H .II I H -: . B C D \ 10% NaOH > 6 100° C ; 6 would most likely be. 0 ll (1) CH3zMgBr / > H (2) H3o+ H 3 CH3— C— H CH3— C—H CH/ \ H I l 3 CH3 CH3 A c CH \ 3 0:0 \ CH3/ Questions 9 - 15 concern the reaction of substrate Y with the reactants shown. 0 II Ph/C\ CH3 Y ; 9 would most likely be Et H 0’ ' ‘I’H ' I? Ph— C—H Ph— C— OH I Ph— (IZ— OH I Ph— 0— Et CH3 CH3 CH3 A B G) D excess I I OH OH > 10 10. ; 10 would most likely be HO H O | (EH |/> <"3 Ph— C—H Ph— 0— O C/ | Ph— C— OH | Ph— c— 0 CH3 CH3 CH3 ; 11 would most likely be HS H S \- I ‘1’“ I a.) 3 -. x __ _ _ _ ‘3 Ph C H Ph— c— SH Ph IC S Ph— c— s 3 I CH3 ‘_ I - CH3 ' B C D 10% NaOH ——> 13 13. ; 13 would most likely be_ Ph H\(|) H E Ph CH | / 3 ’ Ph— \Ph >c= C: Ph CH3 H H3C Ph ; 14 would most likely be I (ll $H ll 1? h) Ph— (|:— C1 Ph__ C_ C1 Ph— 0— 9:- c1 Ph_ C_ C1 C4 CH ' H 3 CH3 (1) CH3CEC2Na 15. ; 15 would most likely be‘ ‘PH 913 C C I” I C Ph— (ll—*H Ph— c; (3— CH3 Ph— CE 0— 0— CH3 CH3 CH3 ® B c » CH ll \C= /C\H (1)0H3Li> 1 CH3/ H (2) H20 ; 16 would most likely be Oil-13 }|{ E CH3 (I')CH3 \ CH3 ?H CH3- C— c— C—H c: c— C—H CH3\ /H ' ‘a \c— c— C—H I ' / ' ' C= C=C / — I I CH3 H CH3 H CH3 / \ ‘- ‘ CH3 H CH3 CH3 CH3 C? B C D _ 1) CgBr —_ E E H ICIi 2) H20 17 17. Compound 17 is most likely . A \c/ \H / E D A] 1)Li(CHs)2Cu 18. Compound 18 is most likely . 19. Jimmy added NaOH to a solution of 19 at 5°C. Earl stormed into the lab. Earl was cross that Jimmy performed the reaction without him. Earl cried “Bo, you coulda waited”. Jimmy said “I waited for an hour for you to finish watching ‘dukes of hazard’. ” J immy kept the reaction mixture cold and isolated the product. Earl was like "Dude, keepin it cold produced ". 10% NaOH F -~ 0 O II II b — 50 C 5 7, v1 19 0 D. 121 mixtreoanndB \ E. A 1:1 mixture ofB andC ’l‘ob S-‘(fm 0L 20. Jimmy added NaOH to another solution of 19 at 5°C. As he was watching, the cold reaction mixture changed from a solution to a brown goo. Earl exclaimed “Cool ! Bo keep it cold and wash the goo with cold ether. I know exactly what you made”. Jimmy added some ice cold ether to the brown goo and stirred it for 10 minutes. We filtered a white powder substance away brown liquid. He discarded the brown liquid. Earl confidently took the white powder to the polymer lab and confirmed his suspicion that Jimmy had created the polymer below where n ranges from 15000 to 20000. Earl said to Jimmy “You made the polymer because .” R) A. you’re an idiot D. you are incompetent as a chemist . the solution of 19 was too concentrated E. the solution of 19 was too dilute . your thermometer was off by 95°C H /C\/\/C C C\CI_I3 21. Aldehydes are more reactive toward nucleophilic attack than ketones because CE ketones are typically more electron rich B. more than one resonance structures can be drawn for ketones C. aldehydes are conjugated D. ketones are cyclic E. aldehydes are planar 22. Optically pure ketones that are chiral at the alpha carbon can be racemized when exposed to basic solution because . A. ketones are less reactive than aldhydes B. there is no ring strain . condensation reactions have a carbocation intermediate . an achiral enolate is formed E. a chiral enolate is formed 14 Jimmy told Earl that he oxidized ethanol to the corresponding aldehyde with "organic" chromic acid in methylene chloride solvent. Earl took one whiff of the product and excalimed "I'm quite sure that you used "aqueous" chromic acid." Jimmy retaliated "How can YOU tell from just a whiff? Are you some kind of fragrancologist?" Earl cahnly replied "No. I've been paying attention to those sterling organic chemistry lectures". " 23. What did Earl smell that convinced him that Jimmy had accidentally used "aqueous" chromic acid? A. The sweet fruity aroma of esters. B. The sweet, but pungent aroma of aldehydes. C. The stench of thiols. ‘ ® The sour odor of vinegar. E. He actually detected no odor. Suspicious Jimmy demanded more proof, "OK wiseguy, prove to me that I used aqueous chromic acid." Earl took a 1H NMR of the product. They noted a singlet near 3 ppm as they both expected and a 1H singlet near 11 ppm as they BOTH expected. Earl said "Look at that singlet near 11 ppm. That is clear and convincing evidence that you used aqueous chromic acid. " J immy said " On the contrary, my former friend; that singlet is clear and convincing evidence that I used organic chromic acid." 24. The proton NMR seem to cloud the argument more than clarify it. How could the 1H singlet near 11 ppm be interpreted by both as evidence in their favor? Q Carboxyilic acids and aldehydes have a singlet in that region. B. Esters and methylene chloride have a singlet in that region . C. Thiols and alcohols have a singlet in that region D. Water and methylene chloride have a singlet in that region B. Thiols and water have a singlet in that region. 25. Earl had just about had it, but he saw Jimmy's point. The 1H NMR was not very helpful in this case. Earl did not let his lack of confidence show through "OK Jimmy, let's take an IR spectrum of the product and I'll bet one of those rare eagle quarters that we'll see in the spectrum. This will prove to me and the whole world that you did use "aqueous" chromic acid. A. the two peaks characteristic of a primary amine near 3400 cm'1 B. the meta-disubstituted pattern between 650 and 800 cm". C. an intense peak near 1700 cm'1 ’ . a smooth broad hump near 3300 cm'1 ha I L “is; ' a broad hump near 3000 cm'1 that is jagged at the bottom’ CM "7 I . < r I + r pm I" 0"! Laulé I?" 0 5M3 6 mg ‘0 l1 «M‘fia O r . 3 n 'O-‘/‘ 6/ ens -’ C. P” .. a,” ’ r r 3? CH3 ) mm» W o 5%,} m“, W . H V H d «mL Czk/dhfl' «ML fl QAKM“ my ) C YE v on, H ( pct .k cwzclL) ...
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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 2001 test 3 - Chem 228 SSII 2001 Test 3 Dr. Wells...

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