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Fall 2004 test 2 - Chemistryr 22’ Test 2 Organic...

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Unformatted text preview: Chemistryr 22’! Test 2 Organic Chemistry Test 2 Name 1 g e“ E Score = opscan* sens + essay = ['3 * 81} 1'13 + 115 = H“) F" Nil-Ll“? do“; I! Essa}F A. 11".] points. Write the complete mechanism (show electron pair movement with I curved arrows for each step} for the E1 reaction below. - Draw all lone pairs of electrons. — Identify the rate determining slow step and an},F fast steps. - Draw the produet[s}. 5‘ *HI’L... h 1'1 - Write the rate equation for the tion. (Le. rate = k.......} reaction H3 1: OH _ CH3 mechanism CH3 {-‘Mh .4 G3 | f“!- slo” *. , 1 '. CHq—f—i' h- C: H ___,.. C. .- i . t"? cLb , '5 \fi Cii ”H 3 H! L}. 1" Essay 3 . It] points. Write the complete mechanism {show electron pair movement with curved arrows for each step} for the 5N2 reaction helow. - Draw all Ione pairs of electrons. - identify the rate determining slow step and an}; that steps. - Identify an}r intermediates {with [ ]} or transition states [with [ ]i} — Draw the product[s}. v Write the rate equation for the substitution. (Le. rate = it .......... J reaction mechanism {AA/5 Cl Kate 1 RECEHQLH 1.5 [DH-"l Chemical 8: Engineerin News Octet-arts. 2004 1|ttolurne 32, Number 42 p. 45 Sulfanyl alcohols are culprits in smelly armpits The typical smell associated with A g the human armpit is caused by a witches“ brew of molecules, including steroids, fatty x NEH acids, and sulfur-containing compounds. The sulfur compounds are the most ‘ malodorous, but little has been known about them, until now. Research groups at two‘s" (-53} h fineness and flavor companies have so any! identified these compounds as alcohols [Chet-n. Bffldfvgrd'igl', I, ltifl and lilfili (Etllldfl. .t't team led by DH Anthony J. Clark at Firmenich found eight sulfanyl alcohols in sweat from exercising volunteers, including the major component( P‘ JG- methyl~3—sulfanylhexan-l-ol {shown}, which has an onionlilte smell that is likely the ”most important contributor to the typical and repulsive sweat malodor." A. second team led by Andreas Natsch at Givaudan Schweiz also identified [this compound], as well as three additional sulfanyl alcohols with equally pungent odors. Both teams identified Comeoocterlnm, Staphylococcus, and other bacteria dtat {iWBil in the armpits and produce enzymes that convert precursor compounds in the initially odorless sweat to the stinky compounds. The Givaudan team also showed that the sulfanyl compounds are derived from compounds that contain the sulfur-based amino acid cysteine. l. The compound pictured is best named . A. t R jt-3-methyl-3-sulfanylhexau-l-ol EB; { S 1—3—metl1yl-3-sulfanylhesan- l-oi B C. { + }-3-med1yl-3~sulfanylhexan-l-ol I}. If —)w3-methyl-3-sulfanylhexan-l-o1 E. not enough information 2. The two research teams performing this ground breaking research were from E A. France B. England C. Germany III. USA ® Switzerland 3. The Staphylococcus bacterium, makes the eptically pure sulfanyl alcohol mat is shown. In the laboratory, scientists attempting to make this alcohol by reacting optically pure Sumethyl-B- bromolhexan-l-ol wide NaSH obtained a the racemic sulfanyl alcohol. Why? (3' the reaction followed the SN] mechanism {5 r If 3-:- R )i E. the reaction followed the 3N2 mechanism P‘ C. the reaction followed the El mechanism D. the reaction followed the E2 mechanism E. not enough information C) H 4. Anodier group separated the two enantiomers from question 3 and noted that one enantiomer was indeed malodorous while the other had only the faintest aroma of cantaloupe. Suggest a reason for this difference. A. The compounds have different vapor pressures. B. The compounds have different molecular masses. [3. The compounds are constitutional isomers. D. The compounds have identical boiling points. Ddor receptors are chiral. Ni” 5. This molecule is best described as _ . A. mean and chiral (:9 mean and aohiral . not mean and chiral D. not mEHo and achiral E. none of these ft. This molecuie is host named A. fluoroiodocerhon B. 2,3-diflnoro—2,3vdiiodohntsne C. (2R,2R}+2,3wdiilooro-Efidiiodohniane 6 D. (2.522.5]—2,3-difluoro—2,3-diiodobntsnc (ER,253-2.}-diflnoror2,3-diiodohntsne If. Scnlemic means ’L. . nu” fl ‘ A. hofl'i enentiomers are present 1n equal amounts r” ( ® both ennntiorners are present, but one is more abundant than the other -*‘ S 1:. “I" h ' t” (S C. both cnentiomers are present, but the ratio is not knoWn .._ 7 D. a mixture of diastereorners 1R .- E. a single ennntiorner is present 1L --. .3 ‘0 -}-I LJLL) 199- rt. 3. Consider flue planer conformation of our good friend methylcyciohexane. Which We could he rcpiaced with a second methyl group to give a dimethyicyciohexenc that is chiral ? 9. ENE mentions of the type Nu‘ + RL -m} We + L' are favored A. when tertiary substrates are used 7‘; ® by high concentration of the nucleophile. f ((5 C. by using a polar protic solvent 1" D. h}? the use of weak nucleophiles 7|; E. by none of the above it]. Which of the following statements is true of 3N1 reactions of alka halides in general ? A. The rate of an SNl reaction depends on the concentration of the alkyl halide. fl if. E. The rate of an 5N1 reaction depends on the concentration of the nucleophile. 7;. C. SN] reactions ofaikvl halides are favored by polar solvents are @A and C onlyr are true. E. A. B and C are all true. 11. Which alk‘vl halide substrate would you expect to undergo SN] Inost rapidl},I 'i' a. [cruises n. (cashew C. {CH3 )3 CEI‘ ‘3 ® (ember é‘j Betsy would all react at the same rate LII-edit“) j (db-if) 1 ‘o mi i Consider the reaction of hutyliodide with CF ion in DMF solvent for questions 12 — l4 CH3CH2CH1CH31 + Cli— - ------ 3' CH3CH1CH1CH1CI + 1— [reaction 1) 12. How would die rate ofthe reactien change if the chloride concentration was tripled? A. no efl'eot 5 N L B. rate would double C (E) rate would triple {fl *4. ’3. D. rate would increase by a factor of 9 E. rate would increase by a factor of 2? 13. How would die rate oi reaction 1 change if Etr' was used as the nucleophile instead of C l— “in! a. P1” lit-.31. 2 ML... ‘r—‘tw fl IA. }__ g A. no effect C199 rate would decrease I"JC. rate Would 1ncrease u. in fie?!" if"! L S“. Uta; l4. How would the rate of reaction 1 change if ethanol was used as solvent instead of DMF? Ft. no effect a rate would decrease C. rate would increase Pa Ht. serum #3 new. PM 1-5. Compound G life's iin" optic-as} motion elf—14". Bonipdund H 1's its enaniiomer What is the opiieai rotation of a mixture that was made by“ mixing ID m] G with 2? m] H ? A. —3. 3° 3—5.2" c e . 2’} ,. i O C gym“ e E 49.9" 2;} 1* M) E. +5.2“ 16. What would be the major product From the reaction below ’5' +Qfi Lilia) ‘ Li" on C96“... 7L CH (3:11: H ”NH!" 1-— 3 i: 2} CH3Br CH; CH CH3 fag Br /CH3 \3 /Br I \ . core—or CH..— —CEC—CH3 on .3: on. FL I \3 (H )c/ CH3 on3 x \ CH3 \CH3 CH3 CH3 IT. The maximum number of siereoisomere of 3—ethyi-2-ieopropyl—E—methyl—I-pen wool is 6 @2 n} 3" DH IS. The molecules below are A. identical and meeo compounds E. identical but not mesa compounds _ @enanfi omers ( . diastereomer ...
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