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2002test2 - SC/CHEM 2020 6.0 SU02 Organic Chemistry Sample...

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Unformatted text preview: SC/CHEM 2020 6.0 SU02 Organic Chemistry Sample Test 2 June 13, 2002 Family Name - Time available: 1 hour . PLEASE PRINT Total Marks: 100 Gwen Name(s) Student Number PLEASE ram-r Lab Group (check one): D 99 D Monday El Tuesday [:I Wednesday El Thursday Instructions: Materials allowed: calculator 8:. molecular model of one asymmetric centre. No extra paper. No dictionaries. Use ink pen (no pencils) and answer in the spaces provided. Use the reverse (blank) sides for rough work. Clearly cross out anything you do not want marked. Use the mark value of each question to allocate your time. Keep your eyes on your own paper. 1. Give systematic (IUPAC) names for each of the following, specifying geometry (m as appropriate. (9 marks) (a) 9 Br 5- bmw-o - *l-efihyl kt): — l— at « A 3 03) CH“ 3 weal?! — 2,—( 2m". £357") LilcloPa-t- hex. :. (“20 I 31% l (n+- 212A;- 4- w: (c) H_ . % P a’ r - >\ 2. Give a specific example of each of the following, without using generic groups (R or Ar). (6 marks) (a) a mesa compound (b) an internal alkyne CH 3 p B r H‘ C "" C, 3 C. "" C. “'3 3 H Br 439+; 3. Label the indicated carbons as R or S. (5 marks) E1. , SCICI-IEM 2020 6.0 SU02 Test 2 page 2 of 4 4. Predict the product(s) formed by the following treatments, indicating stereochemistry where appropriate. Indicate if pairs of enantiomers are expected. If no reaction is expected, write “NR." (24 marks) (a) T: ~a*m- (J13 012% (Fischer protection} Cal-C “.3 (b) CH3 «if. CHeQ-ia fig CH3 H1 B! n 001's a ,I CJI'LCIL? ow; (Macaw—3 (C) Na‘m— [ > 0” — " " NI2 5. Draw the repeating structure expected from the free-radical polymerization of phenylethene (styrene), PhCHzCI-lg. (6 marks) r 5k 9"? - H H "if; Frl‘ l-L film I _ ___I “L094 f’? HHNH H SCICHEM 2020 6.0 suoz Test 2 page 3 of 4 6. The following reaction sequence generated optically active product A, whose rotation of the sodium D line at 25° was -23.5° using a 1 dm cell containing 12 g of sample dissolved in 10 mL of ethanol. If optically pure S-A has [0:]D25 +39.2°. what is (i) the optical purity of the product obtained in this reaction and (ii) the proportion of R and S enantiomers obtained? r N: l Ex] ~23 .5— (10mm) 3 a : —_—'__... _ _ . /\/L/ CHaCHaCH /\J\/ "1* C'3Ha£) h )0, 5' A 0- : "far ’6 5 9/ ._._ _\g_ [2-5 : 573% Q+$=l9033 P 34,; go a file ifs H's 2F—= 15'0’4 p" W4 fl_-;: 153/} CAM-€53 . 5:153: 7. Give a complete mechanism for each of the following. Include clear stereo-chemical detail, charges and by-products. as ”Pma‘e' “as (14 marks) (a) The reactionof 2R.3R-dibromobutanc with Zn in acetic acid to give Z-2«butenc. ER ‘0' H duff (—be + z“ __#> Cl; Br 0:) gt: 2 Br Br: ‘ ' racemic 6W" 0.12% Br cl" 9" r, “%‘r a \\ SC/CI-IEM 2020 6.0 SU02 Test 2 page 4 of 4 8. Give the reagents or reagent combinations in the correct sequence to effect the indicated transformalions. More than one step may be needed. No intermediates are needed for full marks, but they may allow us to assign part (10 marks) marks. (b) H H u, : racemlc 9. Clearly indicate which of the following pairs of reactions should occur fasten" __ (8 marks) (a) (DI-£36! + HQ —> (DI-[30H + c: or CHaCI + Br —r OHsBr + of (b) CHaCI + H 20 —> cl-Iacu-Iz+ + Cl ‘ °{ CH501 + H0' —r OHscm + or + ZnBrz I Br (c): BerI-OH' —‘+ M+ Bl". +OH —> HOW/W (d) 0/ +Zn-—* O+Zn3tz 1-0:: +Zn—P 0 “"Br [0. Identify the relati tions 1p wéen the following pairs of compounds as being either the same, enantiomeric or diastereomeric. (a) (b) (8 marks) CHa f. GHZGHs 01%042043 CH" OH H Fh H H3 H Manages CH3 H1 SM (0) P“ F“ (d) 043 H CH5 H H OH 0-13 0-13 ...
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