Test_1-solutions

Test_1-solutions - {0% be. .. CHEMISTRY 2020 6.0A...

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Unformatted text preview: {0% be. .. CHEMISTRY 2020 6.0A FALL/WINTER 2010/11 NAME 5 b STUDENT # TERM TEST #1 (1 Hour) Friday November 5, 11:30-12:30 pm Circle the correct answer in multiple choice questions Answer ALL questions on these sheets. DO NOT USE PENCILS FOR FINAL ANSWERS A partial periodic table is given on the last page (page 8). l.(a) Assign the correct formal charge to each nitrogen atom in the following Lewis structure. “ - + l' (4 marks) $ .. . .' 4‘. 1 ... .- ‘ ' t . . us: * - .v' .. (b) Add the appropriate formal charge to each atom in the molecule below. It is not necessary to indicate formal charges when zero. H \ meme (4 marks) / ‘l'\ H H; (0) Structures \, 3 , g , shown below, are resonance structures, and structure 3 is the major contributor to the overall resonance hybrid. H 3:313; («H Hac’E;g* C(H z 3- oil Ct” cm. H H H go? U3 wv‘a or» 1 2. a “KSSKV'QO 5m H . .. salutes Z W“ a re sov wows was“ 4 .5: s (4 marks) CD“ n ((1) Draw the important resonance forms for the structure shown on the next page. (8 marks) 4- / + + 3 LW\$5 ate-k "‘ a" 2. (a) Circle the coplanar atoms in l—ethylcyclopentene shown below. (b) Which of the following functional groups is not present in the HIV protease inhibitor drug called Saquinavir? (4 marks) A) alcohol B) amide C) aromatic Dl aml' I i (c) Provide the IUPAC name of the compound below. (4 marks) 2,3, 6, 7 - 'EB’meb't'h-ylmomme ((1) Label each of the chiral carbons of the above structure with a star. (3 marks) P a swat. o . g simmer \wwk 93°“ “We W) “M: (e) An unknown compound X gave the following combustion analysis for determining C and H content. A 12 mg (0.012 g) sample of X when combusted with excess oxygen gave 18.6 mg of water and 36.4 mg of C02. Determine the empirical formula of this unknown compound. How many isomers are possible for X? (6 marks) Emeldmk 9:0va C2. HS" (QM-G441») “drug‘s Sokug-D- L19 Cq- Hue Z Z \% D‘M—P—rb /\/ )\ 3. The relative reactivity of the 1°: 2°: 3° hydrogens of (CH3)3CCH2CH3 in free radical chlorination is 1: 3.8: 5.0. Provide the structure of each monochlorination product, and estimate the relative amount of each in the mixture of monochlorinated products. (10 marks) 0°- e— X\ XV” °t><\..._.= mum figsoflzs %zo£~l$§ 4.(a) Which of the following terms best describes the pair of compounds shown: enantiomers, diastcreomers, or the same comgound‘? I . (4marks) . . - not?” A B (b) For structure A above draw the most stable chair conformation. (6 marks) \ CM sta‘oi‘mot BM'LE F” 3 QW‘EOMD‘YBCAW R (c) For structure A in 4(a) assign the absolute configuration of the chiral carbons by the Cahn- Ingold—Prelog R/S nomenclacture. (6 marks) 6W5 J \‘ 0‘ ‘\ 0 Wk oft-kw (K wmgawal-Ron ls awe“ 6 ((1) Provide a Fischer projection of (2S,3S,4S)-2,3,4-trichloroheptane. (4 marks)‘ 7 W3 H qfi, DM’S‘D“ (Iii at M W 5. (21) Given that (S)—bromobutane has a specific rotation of +23.10 and (R)-bromobutane has a specific rotation of -23.1°, what is the optical purity and % composition of a mixture whose specific rotation was found to be +184"? (4 marks) Hm WM (“MM (b) The mixture from 5(a) was subjected to reaction with NaOH. Assuming all the products come from an 8N2 process, indicate the structures with the absolute configuration at the chiral centres of the products, and the % distribution of each one. (4 marks) Noon M‘F‘tw’b to $3193 79 Bug-Er Mlo.1%(fi)&‘3r \vt, 3W?— 3 BuBr "‘45 (—EQBKDH .‘ Heme, sis 7° [6) (saw M10110)” V fi/ ii; gq'g 0/0 & [0.10/9 5 (c) If the R-isomer in 5(b) has a specific rotation of [0t]D: —13.90 caicuiate the specific rotation of this mixture. (2 marks) Coll: ——--\\.ob —--\ it mu?) 6. Draw structures for fog; of the five below: (5 marks each) (a) The Newman projection of the gauche conformation of 1,2-dichloroethane. (‘X a: t; “L K M (b) The Fischer projection of 2R,3S-dibromO’outane BY w \0Vl (c) Bicyclo[3.2. 1 joctane (d) The most stable chair form of 1,3 -dimethylcyclohexane which does not Show Optical activity. )4 H CH3 06 4: (e) 1R,2R—Diethylcyclobutane gr “h M .. u ‘ a. 14 THE END é Carbon 217 12.910? '_ " ...
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Test_1-solutions - {0% be. .. CHEMISTRY 2020 6.0A...

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