2004test2 - :r n “0 | u f" 7'7 J “a L 2’ CHEM 2020 F04 SC/CHEM 2020 6.0 F04 Organic Chemistry M1 d-Course Test Family Name r Friday ‘

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Unformatted text preview: :r- n “0%.; | u .. f" 7} '7 \ J “a ' L 2’ CHEM 2020 F04 SC/CHEM 2020 6.0 F04 Organic Chemistry M1 d-Course Test Family Name: _ r __ Friday. December 17, 2004 ‘ PLEASE 93‘?” Test value: 209.; Gwen Name: EASE Inge—York ID #: _ _ Time available: 120 min PR' fl Lab Group: CIRCLEUNE 99 Mon Tue Wed Thu a.m. Fri Total marks: 100 ' Instructions Material allowed: calculator, S-atomM-bono model. No dictionaries, no extra paper. Use ink pen only (no 1, Use the blank pages for rough work. Cross out material not to be marked. Use the mark value of each question to pencils allocate your time. Stay seated Et quiet until all papers have been collected. Keep your eyes on your own paper at all times. 1 . Give systematic (IUPAC) names for each of the following: [4 marks each = 12 marks total] (or 7/7 . 1 we: (a) C/QHa Hag Ca ‘9 ‘T "Pan 'l kip-f"! 2:5 " an — {yMé .r‘ label as E or Z label as R or 5 ES)- Cyfiio hog-{3. if! ’ 3 edit—"é U y 2. Give a specific example (without generic groups X, R or Ar) of each of the following. {6 marks] (a) a secondary alkyl bromide {b} a geminal dibromo compound (c) a bromohydrin {D 8? 93" gr u . I ' agar—cab. % Br / H l—Il CH3 FC‘ "CH-3 Il—Cgs-FCLIQ 3. Usingfle pk, values given, indicate, by checking o__f_f_”t'he appropriate box (El), whether the products "OtmieacT‘anfs will dominate therfqllowing acid~base eq'uilibn'a. [6 marks] 3 (a! H—CEC—CHa + LiCHa $d= Li‘ _CEC‘—CH3 '+ CH4 [3 reactants IE/Drodu pK" values: lo 1‘5 5’). "60—" 52 (b) NET—CEC—CHE, + H20 # H—CEC—GHa + NaOH Dreactams moducts . Hie—EC—H 25 5.6.;- / filo—H 15.? {C} (CHalao—OH + KOH .——‘* (CH3536—O_ K71: Ell/reactants Elprod s K'(H3C)3w—H 19 I luv!“ Q1 ’0‘ ‘ "’ l CHEM 2020 F04 4. Predict the productls) formed in TEN of the following TWELVE treatments, indicating stereochemistry where appropriate. Only the first ten answers will be marked. If diastereomeric products are expected, draw them all. If and only if pairs of enantiomers are expected, indicate with "racemic" or "+ enantiomer”. If no reaction_ is expected, write “N.R.”. [30 marks] ,4 {3) Ci) +H 0 O Q 0% [a 25 O; / In acetone 0T3 , A j I in ether _, ,-.. 7' "‘CH3 7 (C) 3' heat _./\!0Ll+3 ., ..._..__.. .,, . ,2 "13H3 in HOCH3 “3 if“?! \k ,z. ,,‘ (d, WET KOH ; 200° - - :7 Bl. PFDIOHQBEI heating "'- - 1 H3 i...) gen. @ m O/CHa 3 (g) (CH3)3C—CEC—CHZCH3 Lindlar’s catalyst " (h) (CH3)3C—CEC-CH2CH3 -——_.._.. in CH BCI 2 If... ..,_, . . la 0 N OH (1) ( 3)3CHCEC_H H2 2’ a 1 .. 7 _--i.. -' ' _ / In ether “‘— L H- \_/ 'ia is sec-isoarnyt {= 1,2-dimethylpropyl or +methyibut-2-yl) l {9 (1 m 0:0 Nam / o H in J I continued on next page W 6 4. {continued} 7 (M OH PBr3 a . f / "'czn3 H c n . .4 /in 3 G CchHzMgBr dilute H30+ (“LLB 0 ———-. —n-——* “01* 6‘ in ether ‘ _:-{i¢.c_-= ,c; t r; a; 5. Give a complete mechanism for each of the following. Include clear stereochernical detail, as appropriate to explain the result, as well as all intermediates, charges, by-products and necessary arrows of the correct kind. 164parks] as _,_t_ (a) The reaction of M-dibromopentane with potassium iodide to give Z-Z-pentgge. Include aglear a; {4' t , x” drawing of the transition state that explains the stereochemical outcome. ” I L ' J” -.i 'Br. H 4; if?) " H . ‘1 ILCH " ‘4’ t H . \.‘ a; ‘ z: ‘ _ __ ‘i‘ H C flc:""6lb_d13 trig H"? H ")5 EB ’ —“—2 2C; — Ci ~ V w 5%” p, 3L \VJ cI.l_ - .’ “" d. _+-'.' . k if]! a}: lngi 544.4% P94) n“ N4 (b) The polymerization of propene, using as initiators (CH3)3C-C+O-C(CH3)3 and heat. Include one Hadfio ermination step. Indicate the correct regiochemistry. ' 11/“ 6’ A . . 0/ 0—0 — a wee—v 2L (dew a 2‘ VFW-hon V/ “#5143 I «VJH; lI-l at]? cl} .fl Pa,“ . . r" “and l. . C0 4_ “Par—m ..._9 ((331290— CH1" g1 ° + . C_=c_H -—9(d-Q_3C --—-CI. ('5' ' H I n H H h” I m'mr-t‘l‘iw I// '_o . i%4é%fiim+ (Cong - c—gc + be? c— Octet; as ON 3,444 ‘l:;;"“ii H r W CHEM 2020 F04 a. A sample of optically active materiai had an optical rotation d 44“ when measured with the sodium D line at 25°C, using a solution made by dissolving 1.2 g in 10 mL of solvent in a 2 dm cell. What is the specific rotation of this sample? [3 marks] _._- [M]; “Elma ._.__- ___-_2—__’iE_——-—- I :1 Caz iii—finch“) 19m 7. Clearly indicate, by checking the appropriate box (), which reaction from each pair should occur fastest. [15 marks] (8} more r'—~ CH38r+F_ c 3 l‘+ Br_ —- CHaBr-l- of (C) D tho —' PhCHIOH; + Cl‘ IE F'h +1433 —' PhCI—lfiHf + oi" “’ tel Era El CH (a) 3 6”“ => @PoDL iirr WA 3GHZCI + H0_ —» CH3CI-120H + 03' El CHaCHzc' + H20—* CHSCHZUHZ" + of (hi HO _ \'/ +Br 8. Give the reagent(s) or reagent combination(s) in a correct sequence in order to effect the indicated transformations. More than one step may be needed. More than one answer may be correct. No mechanisms are required. No intermediates are needed for full marks, but they may lead to part~mast if the intent is evident. [12 marks] 9H3 ’ CI OI Vlracemic) iv \/ [he‘d do“ 75H “0T5 _ ' Era +em-i-iom +emdigr=¥ H0 CH3 lb) 6 3‘ ...
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This note was uploaded on 12/14/2010 for the course ORGO Chem2020 taught by Professor Potvin during the Spring '10 term at York University.

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2004test2 - :r n “0 | u f" 7'7 J “a L 2’ CHEM 2020 F04 SC/CHEM 2020 6.0 F04 Organic Chemistry M1 d-Course Test Family Name r Friday ‘

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