chemistry spectroscopy

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chemistry ch3021a teacher-marked assignment spectroscopy student instructions Overview This assignment is designed to give you practice in demonstrating your understanding of chemistry. It is not for NCEA credit, but it will help you to develop your skills, so that you do well in future assessments. Conditions •• This is a closed-book assessment; you may not refer back to any booklets. •• There is no time limit for this assignment, but allow about one hour to finish it. You will need: •• a pen or pencil. If you do not understand any of these conditions, please phone, fax or email your teacher now. A Periodic Table and correlation tables for IR and 13C NMR spectra are supplied near the back of this assignment. Supervisor requirements You and your supervisor (if applicable) must sign the cover sheet at the back of the assignment to verify that the work is your own. Assessment criteria Not Attempted Did not attempt to complete. Not yet on target for Achieved Did not demonstrate an understanding of spectroscopic data in chemistry. On target for Achieved Identified discrete aspects of the structure of organic molecules using teacher-provided spectroscopic data. On target for Achieved with Merit On target for Achieved with Excellence Determined the structure of organic molecules using spectroscopic data. Justified the structure of organic molecules by integrating spectroscopic data. For teacher use only © te ah o o t e k ur a p o un a m u 2013/1 ch3021a teacher-marked assignment answer all the questions question one From the following mass, 13C NMR and IR spectra shown for compounds A, B and C, give the formulae, structures and names of the unknown compounds. In each case, justify your choice of formula and structure. (a) 100 % abundance 80 60 40 20 0 10 200 2 20 180 CH3021A 30 160 40 140 50 120 m/z 100 60 ppm 70 80 80 60 90 40 100 20 0 © te ah o o te k u ra p ou n a mu ch3021a teacher-marked assignment % transmission 100 50 0 4000 3000 2000 1500 wave number (cm–1) 1000 500 Elements present or absent Molecular mass: Reasons: © te ah o o t e k ur a p o un a m u CH3021A 3 ch3021a teacher-marked assignment Functional groups (present and absent): Include reasoning. Molecular formula = 4 CH3021A © te ah o o te k u ra p ou n a mu ch3021a teacher-marked assignment Possible structures: Reasoning for best fit: Name of compound: © te ah o o t e k ur a p o un a m u CH3021A 5 ch3021a teacher-marked assignment (B) 100 % abundance 80 60 40 20 0 10 200 20 180 30 160 40 140 120 m/z 100 50 ppm 60 80 70 60 40 80 20 0 % transmission 100 50 0 4000 6 3000 CH3021A 2000 1500 wave number (cm–1) 1000 500 © te ah o o te k u ra p ou n a mu ch3021a teacher-marked assignment Elements present or absent Molecular mass: Reasons: Functional groups (present and absent): Include reasoning. © te ah o o t e k ur a p o un a m u CH3021A 7 ch3021a teacher-marked assignment Molecular formula = Possible structures: Reasoning for best fit: Name of compound: 8 CH3021A © te ah o o te k u ra p ou n a mu ch3021a teacher-marked assignment (C) 100 % abundance 80 60 40 20 0 10 20 200 30 180 160 40 50 60 m/z 140 120 100 80 ppm 70 80 60 40 90 20 0 % transmission 100 50 0 4000 3000 © te ah o o t e k ur a p o un a m u 2000 1500 wave number (cm–1) 1000 500 CH3021A 9 ch3021a teacher-marked assignment Elements present or absent Molecular mass: Reasons: Functional groups (present and absent): Include reasoning. 10 CH3021A © te ah o o te k u ra p ou n a mu ch3021a teacher-marked assignment Molecular formula = Possible structures: Reasoning for best fit: Name of compound: © te ah o o t e k ur a p o un a m u CH3021A 11 ch3021a teacher-marked assignment Extra space if required for your answers. Clearly number your answer. 12 CH3021A © te ah o o te k u ra p ou n a mu © te ah o o t e k ur a p o un a m u CH3021A 262 263 264 107 265 108 268 109 192 261 262 106 190 226 105 104 186 223 181 179 Rf Db Sg Bh Hs Mt Ir 77 103 76 103 88 75 101 87 74 98.9 Fr Ra Lr 73 95.9 45 184 72 92.9 44 58.9 27 W Re Os 56 55 91.2 43 55.8 26 11 12 195 197 79 108 47 63.6 29 201 80 112 48 65.4 30 204 81 115 49 69.7 31 Pt Au Hg Tl 78 106 46 58.7 28 10 Zr Nb Mo Te Ru Rh Pd Ag Cd In 42 54.9 25 175 71 87.6 85.5 41 52.0 24 9 13 15 207 Pb 82 119 209 Bi 83 122 51 74.9 33 31.0 I 210 210 85 127 53 79.9 35 35.5 17 222 86 131 Xe 54 83.8 36 Kr 40.0 18 20.2 10 Ne 4.0 He Cl Ar 19.0 9 F 17 Po At Rn 84 128 52 79.0 34 32.1 16 S 16.0 8 O 16 Sn Sb Te 50 72.6 32 28.1 P 14 Si 14.0 7 N 15 12.0 6 C 14 Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br 8 137 Y 88.9 Rb Sr 40 50.9 23 V 7 133 39 38 37 47.9 22 Ti 6 Cs Ba Lu Hf Ta 45.0 40.1 21 39.1 20 Ca Sc 19 K 5 27.0 4 24.3 23.0 3 Al 12 10.8 11 1.0 Na Mg Molar mass/g mol–1 5 B 9.0 1 H 6.9 Atomic Number Be 4 3 13 Li 2 1 2 18 periodic table 13 ch3021a teacher-marked assignment IR correlation table C NMR correlation table 13 Functional group Vibration Wave number/cm–1 Type of carbon Chemical shift range (δ/ppm) alkane C–H 2950–2800 RCH3 8–35 (usually 8–20) alkene C=C–H 3100–3010 R2CH2 15–50 (usually 15–30) C=C 1700–1630 C–C=C 10–40 C–F 1400–1000 CH3C = O 20–40 C – Cl 785–540 CH3(CO)O– ≈ 20 C – Br 650–510 CH3(CO)R ≈ 30 C–I 600–485 R3CH 20–60 (usually 25–40) O–H 3600–3200 R4C 30–40 C–O 1260–1000 C–N 40–60 (usually 37–50) N–H stretch (1 per bond) 3500–3300 C – Br 25– 65 C – Cl 35–80 (usually 40–45) C–O 40–80 (usually 50–65) C–N stretch 1200–1000 H2C = CR2 110–120 RHC = CHR 120–140 C=O 1740–1720 R2C = CR2 140–160 C – HO 2830–2695 RCONR2 150–175 ketone C=O 1720–1715 RCOOR 160–180 carboxylic acid O–H 3400–2500 RCOOH 170–190 C=O 1730–1700 RCHO 190–210 C–O 1320–1210 RCOR 200–220 C=O C – Cl C=O C–O N–H C=O 1810–1775 730–550 1750–1735 1260–1160 3500–3200 1680–1630 haloalkane alcohol amine aldehyde acyl chloride ester amide 14 CH3021A © te ah o o te k u ra p ou n a mu ch3021a teacher-marked assignment what to do next When you have finished this teacher-marked assignment, please make sure that you have written your name and ID number on the cover sheet. You can also use a label if you have one on hand. By post: Put the assignment in the plastic envelope provided. Make sure that the address card shows the address for Te Aho o Te Kura Pounamu. Seal the envelope with tape before you post it. Do not include booklets from other subjects with this Science work. By email: Scan the pages including the cover sheet and email to your teacher. The standard format for Te Kura teacher email addresses is: firstname.lastname@tekura.school.nz If you aren’t sure who your teacher is, call 0800 65 99 88. If you do not have your next set of study materials, contact your teacher immediately. If you are not sure what to do next, ask your teacher for advice. © te ah o o t e k ur a p o un a m u CH3021A 15 cover sheet – ch3021a students – place student address label below or write in your details. Full Name ID No. Address (If changed) authentication statement I certify that the assessment work is the original work of the student named above. Signed Signed (Student) (Supervisor) for school use only assessment www.tekura.school.nz Copyright © 2013 Board of Trustees of Te Aho o Te Kura Pounamu, Private Bag 39992, Wellington Mail Centre, Lower Hutt 5045, New Zealand. All rights reserved. No part of this publication may be reproduced or transmitted in any form or by any means without the written permission of Te Aho o Te Kura Pounamu.
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