ORGO TEST 1 - NAME gflHPl-E QNSM/EU Student Number...

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Unformatted text preview: NAME gflHPl-E QNSM/EU Student Number CHEMISTRY 2020 6.0- SUMMER 2010 1st Class test Answer ALL questions on these sheets. DO NOT USE PENCILS FOR FINAL ANSWERS 1. Give the complete (including stereochemical considerations) IUPAC names of ALL SIX of Ehéc fggggficgfmgglgl? (36 mark8)(s'fl> —I,-z .. Due LLVL. - pm .. fiu‘rvL CW: co ms cc“; 8) 3‘” (sM- 1,2-fi-(1-inemH—5— $‘- (BF “W'SHVL‘E‘WVQ / Give. o muth m vsv Cam-«0* Remnants Tfif fifteen-GEE"ka THE-n: Her-IE c'h bk 8‘5 .“ ‘ :SGIA' 05“ “I Ja~ S‘R u‘m _ 915:0 ,, rte fluff-1913!?!“an QROEA (.5 W#\ug 13) C> BICYCL. 0 5+. .1. Ojbl-IEW’Y’I’QH Js: ' um (51°- ‘ h: ‘IC US“? wart-rs 0900m- .—r u ‘ra v in )H: Lflkfigrv NMth DBDVLT “" "‘5 TH-BV MN 0 ‘.__ Eu {7 . C) mt“ 3'3”? 0 Fun. .cxonfius u- _ 71241.7 EMF, bv‘r fi-HIE' o 5-" Lflq‘3vfil-HETHkaEM‘I-"AMI‘F ’ @ch—CVCLOFRQPV DEDWGV “I 1"“ 3.3 (=le U‘ldi‘lug d) W -n 'FLUOfiO“ é-Bkbnbflu’” I )NVLP'N! (‘7 9- Mrrcz‘rH‘IL" 7" (F’n’r ‘ TRIoEofi-(2E,$E)“b”5”cq ‘ 0R H: :23th MSSWG 1“ (15:13.2 ‘ hIJSI'MQ " 'n W é I ? 7“ —_ w PLuoto—q wound» a (2,: 65% 6-3.20er H,” b! ,°r “J - . ECflOIICEMl-E‘ 6R , ,Tweeow /L)'T"RID _ . (’3 fir (2E (EBuTRiblECISAIfSM/E— "" l QR 3R)-I'~—Bkw—I a. v3 «cum kg- 1-“,EYNL, L M ’ CVCLBPENTY-DM r5: -IHENE -Dihisw—MLHVM _, .. Mwoww—cuwkw-‘SJw (333193 B -Z Ill: 3§ngLR mumw w-K lg 6H5: mugs-246: (5R (gs/(pk) w3~Bfibnhv$utfiflbtRh-3J #40 b [nfirws/L-I—Hexrsnur’f 2. Draw the full molecular orbital structure of cyciopropane. (8 marks) 4 vavs I nut-w PM: Ea?“ 0 yaw-aweom. 5mm“! me ‘S ' s FER 3 <1 GUNS 13 rmth at cEBiToLI BENT 29‘:— m—I 14:404.”) Ho‘r GM 34415 ‘FRIOUC-LG" 0/ ' t mater: pm THE“ gil‘gléoiguu cvfikgnpfitme Turiagpi; ‘ 1‘ 0 17:9 - “ "1-H" AME. Hk‘r NEG erggkq . Trout}. u} a amalluw AT AN AHME- V‘Gi‘ct. 14 PM): 3. Draw the most stable chair conformation of cis -4-tert—butyl-l~propylcyclohexanc. (7 marks) I /\. aw ’ Ll WA cu? “zwccu, 9H3 ,,_GH: €nvE '1 Hbftvcx I”:an win. «ezm/ WM GIVE alt-119%! 7F vfifiv’ Gogol—52c,“ (\2 wmi‘rfi. TM? W—W,u M Jan- /\/~»c(’wzg fiHpm-(CIYIIA 4. Predict the major monobrominated products of the following reaction on isobutylcyclohexane. Name the products. Determine the theoretical yields of the products. Show the Mechanism of the reaction using only One of the brominated products as an example. (24 marks) 11 Br I m V ‘1- ' y rm ‘ Br2 Tequiv. r l,.......r.,._ \ . s ' “‘"M"\ THE\RJE.Y:CAL. Vise-£5 Is :62 EiQC/H. l Ufltk’fi .h \ Wgcpnu?Jr-1® Q) 5”»; PM? " ““ emu-t 0HE~ “3/4 5 2 (gr. w 15:12»!!th W“ V‘" I (D - @Mnrtw CD (5 q 20-119mm Tpgwi'.erio¥rs;u Br _/J_f R I. . A RfL C3 5) Predict the major organic product of the following reactions. 3) "S H i + E —-—---——> acetone 13) NaCN I --------—--—>— acetone \__n—._.. Br .‘ C M a... c) H H2804 ——-“““‘—~'b— 5‘ 59¢“ (20 marks) d) Gnu/ii 9 rat-It. cg QNq cutawao‘r QLW'EK’H-c “20 bra Tr“; QLL‘GUQL‘ 6) (-) Tartaric acid has a Specific rotation of —12.0°. Calculate the Specific rotation of a mixture of 60% (—) tartaric acid and 40% of meso tartaric acid. (5 marks). ~—~7.1° THE END ...
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ORGO TEST 1 - NAME gflHPl-E QNSM/EU Student Number...

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