02_mid - W02 Sec 02 Chem 266 Chem 266 Midterm Test Time 50...

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Unformatted text preview: W02 Sec 02 Chem 266 Chem 266 Midterm Test Oct 23, 2002 Time: 50 minutes On the computer card, circle the best choice A to D for each of the 20 questions which follow There is 1 mark for a correct answer and 0 marks for an incorrect or missing answer. Under ID number, put your ID number Under Section number, put 002 Under card Number, leave blank. Remember to put you name and course number on the right. Calculators and/or molecular model kits may be used by individual students but many not be shared around during the examination period Note: 1) You must return the question paper at the end of the Exam 2) Only the answers marked on the computer card will be counted (regardless of what you may have marked on the question paper). (13) (14) (15} (16) (17) IIIA IVA VA VIA VIIA Atomic Number 5 6 7 Ag SYMBOL B C N 107.9 Atomic Weight 10.81 12.01 1401 Nitrogen (5) (6) (7) (8) (9) (10) VIB qu vms VIIIB VIIIB IB 104 105 106 107 108 109 Unq Unp Unh Uns Uno Une (261) (262) (263) (254) (265) (266) Francnum Radium Actinium 1 W02 Sec 02 Chem 266 2 1. Among the species 1 to 4, in which no unshared electron pairs are shown, the one which has a different number of valence electrons than the other three is NH3 - CH3 No+ F- 1 2 3 80 (Z) 4 ['1 (lg A) 1 B) 2 @ D) 4 2. Which of the following could not be a resonance structure of CH3N02. IT! :EIS:_0. hi :El5:: — ITI ..ll.. 0- _ lfl =.|.:: A) H-C—N=O.. B) H-C—N- : C) H-C—N— : H—c=N-o-H lI‘I + A +2 " A “l” u + " 5 5 670 [719' 020 3. Two and only two Sp2 C atoms and one sp C atom are found in A)HCEC-CH=CH2 @HZC=CH-CN C) [>=o D) HCEC—CN I 7 029 7 7 070 4. Which of the following would be linear? (In each case you should write a Lewis structure before deciding.) .HCN B)SC12 C) H202 D) OF2 ‘lo 020 5. The compound lacking a tertiary (3 °) carbon atom is: A) 2-methylbutane C) 3—methyl-1-butene B) 2,3-dimethylpentane @j) 2,2—dimethylbutane Q 0) C70 6. Which of the following compounds would have the highest boiling point? A) CH3CHO B) CH300CH3 ©CH3CH2CH20H D) CH30CH2CH3 8 979 8 "I ”70 7. Consider cyclic isomers of formula C4H30 having no alcohol groups — i.e. the oxygen is an ether oxygen (C—O-C). The maximum number of possible structural isomers is A)2 B)3 C)4 @4 1L, 020 3-8 '70 3C9 ”7:: 9* 907:3 W02 Sec 02 8. The pair of dimethylcyclobutanes 8625®l£7fl| mflfl which represents enantiomers is C) 27 ’17 m 7, D) fl i7 9. The Newman projections below represent, H H OH H3C NH2 Ph H Holfiaph HZN CH3 H I 7%) different conformations of the same molecule a pair of structural isomers 13) b/w a pair of diastereomers /6 02,13) a pair of enantiomers 10. The pair of compounds which are CH2 / \ A) CH3CH2CH3 and CHz-CHZ /O B) CH3CH=CH2 and CH2=CHCH3 structural isomers is? Br\ [H 07;, @ EKG—C‘H and B B D) rRFC: r and H H 11. The Fischer projection which represent (S)-2-butanol is? Chem 266 3 I Br\c=c:|;r 83 % H H Br IC=CZ Br H W02 Sec 02 . Chem 266 4 12. Consider rotation around C2 to C3 of 2-methylbutane. With respect to this rotation the population of molecules is distributed between the staggered conformations which represent energy hollows. The number of such energy hollows which exists is [0 “b A) one energy hollow only g 5070 @ two hollows of lower and equal energies and one of higher energy. g; 0/0 C) two hollows of higher and equal energies and one of lower energy. / 3 0/0 D) three hollow, all of different energies. 13. In the molecule of mesa-2,3—dichlorobutane suppose an exchange is made between the C— 2 hydrogen atom and the C—2 chlorine atom (models or a Fischer projection diagram would be very helpful here). The resulting molecule would be best described as A) still meso B) achiral C) racemic @ chiral {{90 a; 570 14. You have the following three stereoisomers of tartaric acid, HOZCCH(OH)CH(OH)C02H 2R, 3S 2R, 3R ZS, 3S and from them, four solutions are made up containing. 1) 2R, 38 only 2) ZS, 35' only 3) an equal molar mixture of 2R, 3R and 2S, 3S 4) an equal molar mixture of 2R, 3R and 2R, 33 The solutions which would rotate the plane of polarized light are @ 2 and 4 only B) 1 and 2 only C) 1 and 4 only D) all ofthem 147070 019% 51/070 15. The chair and boat forms of cyclohexane are best described as a pair of: A) enantiomers B) diastereomers @onforrnations D) structural isomers all 076 16. The most stable conformation of cis-l-tert-butyl-3-methy1cyclohexane is the one in which: A) the tert-butyl group is axial and the methyl group is equatorial U 075 B) the methyl group is axial and the tert-butyl group is equatorial C) both groups are axial 5 3 a} D) both groups are equatorial W02 Sec 02 Chem 266 5 17. The compound sec-butylamine is MD 070 CH3 A) (CH3)2§CH3 C) HQNCHzéHCH3 2 6 076' NH2 9H3 B) HzNCH29H2 [email protected] CH3CHCH2 5’ CHZCH3 {\le #070 H3C\ ,CHZCHg 18. The unsaturated alcohol shown is correctly (IUPAC) named as: ,C=C H 30 ‘CHZOH 7-6 7' A) 2—methyl-3-methanol-2-pentene 66% ® 2-ethyl-3-methyl-2-buten-1-01 C) 2-dimethylethenyl- 1 -butanol D) 3-hydroxymethyl-4-methy1-3-pentene 19. The number of chiral carbon atoms in the steroid 50t-cholest-1-en-3-one is: CH3 CH 3 CH I l 3 CH(CH2)3CHCH3 H3C 70/ H O A) 5 B) 6 C) 7 @ 8 W70 W70 H170 36°70 20. The symbols R, S/ E, Z for the configurations at the ring carbon atom bearing the alkyl side chain and at the ring carbon to carbon double in 50t-cholest-1-en-3-one (Q 19) are: @112 B) 12.13 C) 5,2 D) 3,15 173”?- 1/070 9290 Chem 266 Midterm 27-Oct~02 Total Possible Points: 20 Students in Group: 236 Mean Score: 13.03 65.2% Lowest Score: 2.00 10.0% Highest Score: 20.00 100.0% Standard Deviation: 3.02 Variance: 9.14 Measure of skewness: -0.33 Degree of Kurtosis: 0.41 Reliability Coeff (KRZO): 0.62 Number of Students who passed: 206 87.3% : I oo (>o.10%) I 02 (no-30%) I 03 (80-40%) " - o4 (>4o-50%) I 05 (>50-60%) a 03 pea-70%) I 07 (no-30%) I 03 pan—90%) on I 02 03 ...... _ _ 620-2) PM) 96-8)__.(->. _RawScoresl Iii} :.:.: - ...
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