ORGO TEST 3 - NAME Sbh'éri 0W9 K fié STUDENT CHEMISTRY 2020 6.0 SUMMER 2010 TERM TEST#3(2 Hours Wednesday:30—1:30 pm Attempt a_11 questions

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Unformatted text preview: NAME Sbh'éri 0W9 K fié STUDENT # CHEMISTRY 2020 6.0 SUMMER 2010 TERM TEST #3 (2 Hours) Wednesday July 14, 11:30—1:30 pm Attempt a_11 questions Each question except for Q.17 and Q.18 is worth 5 marks. Q.17 and (2.18 are worth l0 marks each. Circle the correct answer (no explanations required) in multiple choice questions and fill in the blanks where indicated Total pages 8 including data sheets Atomic weights : H—l; C-12; 0-16;N-14; 3-32; (31-35, Cl~37 (1:3); Br~79, Br-Sl (1:1) 1. Which of the following would not have a C-H stretch at about 3050 cm‘l? A) 1-pentene B) 2-pentene Q C) 2—methyl—2—pentene 2,3-dimethyl-2—pentene 2,5 - &\MH~1L'2‘QQ’AW /\l§/\ 1° (“4C E) 2,4-d1methy1-2-pentene l 2. Deduce a possible structure for the compound with the IR absorptions below. 2100 M4 F C3H3Br. 3300, 2900, 2100 cm 1 H way 3 r A "1 it. lfi 0O W “530° a..." 3. A nonlinear molecule with n atoms generally has 3“" ‘5 fundamental vibrational modes. A) 2n B) 2n - 2 C) 3n D)3n-3 4. In a mass spectrum, what m/z value would correspond to the following fragment? (next page) +2.. Cat-£902, M: {+23 but 22— .c'aoo . __ 1 H30 5. Which of the following structures is consistent with the mass spectrum shown below? 100 M 90 Ba - 1’0 6.0;! 513 - 40‘ Relatinélntmsity 1D“- ' a: 4-0" .20: 3'01 46' 5'3 so 3m so": '90 mo- 03A M55 \‘\ MIG-1W5 6. If the mass spectrum of chlorobenzene shows a peak with an m/z value of 114, having an abundance of 15%, calculate the m/z value and approximate abundance of the molecular ion Peak Chas LL Foray-UL was: we; w eh». M/Lzll‘r Wat Coft'eagouk are Ca. 65 $C$L zgmfh '1 3:\ , thzgor M/‘Z-T: Hz is 3); inimsl—lyogs Sub-taut 3 M5 g“ Mgfimwzangws -_-; 57° Was: u‘r 7. Using a 60-MHz Spectrometer, the protons in dichloromethane appear at 5.30 ppm. When the same sampie is placed in a 100—MHz instrument, where does the signal appear? A) 8.33 @423 grew *6» Mt CW “9* We *W'S“ D) cannot be determined from information given 8. On a 90 MHz spectrometer, calculate the frequency downfield from TMS at which a proton absorbs if it appears at 4.20 ppm. \p‘awc ‘3‘- ‘10 Hz. prwg'leuxr‘g‘rom’l-‘HS PG: 4'29 efwk 9m’C-DK shawl» out 3—1:? H; Abram-Stem sneezing. gulo’me’C '5 WK‘J‘ is LAM—3.5 M H 2. u it”; lit: Luam 9. Predict the number of signals expected in the proton spin decoupled 13C NMR spectrum of the compound shown below. 10. Why is carbon—hydrogen splitting not a major part of 1H NMR spectra? no abuwm ‘75 , ‘ZC mt aclw§ 11. What comound exhibits only two signals in its 1H NMR spectrum, a triplet and a quintet? A BrC CHZCHzBr V B) BrCHzCH2CI-I2Cl C) (CH3)2CHCH(CH3)2 D) CH3CH2CH2CH3 E) (CH3)2CH0CH(CH3)2 12. Predict the number of signals expected, their spiitting, and their relative area in the 1H NMR spectrum of 1,2-dichloroethane (ClCHzCHzCl). Ghee .33sz new Ck. 13. How many peaks appear in the proton spin decoupled 13 C NMR spectrum of the compound below? 14. Provide a structural representation of cis—3 ~ethyl-1,2-epoxycyclopentane. D “g Sgor WW SsxexRoQM/CM' 15. Provide the major organic product of the reaction shown below. (Include stereochemistry) . 0H 1. that! 2‘ aflficuzcm 16. Suggest a reasonable mechanism for the reaction shown below. Br. (whims-=83; 01—1 W Jr ‘15 $31. a 0%“ 17. Provide a structure for the expected product of the following reaction. Include the stereochemistry of the product. (10 marks) 1mg" - eat-t oer . 0 W3‘“‘ 1;: “3% 3) H 0* 3 “.2 WM gm- MWVLS SAVQPQDQMEM “B Mick-1 €08“ a“): Mfi‘ Sub-st. manom- 31:03 5W®‘“‘S Xvwaxeipw , M2 fguhm mks ‘55 lulu—bug 5\Q.r°.o LL 18. Provide a structure that is consistent with the data below. (10 marks) BMW C9H7Cl IR (cm-1): 3050, 2950, 2220, 1620 1H NMR { d): 7.8 (2H, d), 7.2 (2H, d), 2.1 (3H, s) 13c NMR (d ): 140 (s), 132, (s), 125 (d), 122 (d), 88 (s), 83 (s), 18 (q) fl -— / Inn-no 1:: n— CL \ I azg—m3 or (2.113 '2} C...Q 02 V1...“ M9430): __,.C\_ mks SYN“ my D'HAP‘V skbsi'itw‘c'xom Fatth ow \DE—VKZ‘ENUK 6% 69“}: Wk; 2691(— —C"':.'=.Q."" "\‘Z <9 +1 THE END Col-reiafion Chart of Typical 1R Frequencies for Gammon Organic Functional Groups ,W, , ..... . r i , i 1‘ EH Smholswqrmls; . Fm .fi[<?§¥b9¥¥fi9§9ids “ $.17”? w i 7 355973?99(§’9F9“§2m ‘ .. .... ._ , 73209??2.509..(Y'P¥°a‘?. . zéaigmdesvfimwmmdfif ‘ “9100-3929191” ._ ' Two bands 2850—2695 (“I - _ 2260—2( ' 21096;). 7 Two bands 1850—1) h n ..1..?9°:17‘?“(m3 ISIS—fights) ' 7 east-chm ~ ._ Eamlieaéids 9?..5Fstfifi,§qt-afiphaac " .9“??? ...... .élfifiéfF‘E-‘f: ________________ __1719:1720(s) ” |C=O' .165!st (m). f . ~ ‘ A A mama-50471147515)- Fm“ mmm‘is : ' 1360—1290(3) _ 13.9%:19999) . T 1 GO. .Alwhflfi , ’” 5: strong, m=mediuni, w=weak, v=vatiable Proton NMR Correlation Grid PPm Carbon-l3 NMR Correlation Grid ...
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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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ORGO TEST 3 - NAME Sbh'éri 0W9 K fié STUDENT CHEMISTRY 2020 6.0 SUMMER 2010 TERM TEST#3(2 Hours Wednesday:30—1:30 pm Attempt a_11 questions

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