Spectroscopy Problems Part 1

Spectroscopy Problems Part 1 Introduction to IR and Mass Spectroscopy
Dallas K. Bates Michigan Technological University
This series of problems has undergone several iterations over the years. I would like to thank former students of CH404 and CH4412 for their interest in spectroscopy and their helpful comments on spectral data presentation and interpretation. The changes I have made to drafts over time were driven by their input and interest in solving spectroscopy problems. There is no greater motivator for an instructor than a classroom full of active, inquisitive minds. I would also like to thank my graduate students who have discovered many anomalous reactions that have become fertile ground for new spectroscopy problems. I would especially like to thank Geetha Boreddy, Anil Ekkati, and Parag Jog who recorded many of the original spectra reproduced here. They have always been so ready to help out with any task I suggest and so gracious and generous with their time that it is impossible for me to adequately express my thanks. If you have any questions or comments about the material in this text, feel free to contact me at dbates@mtu.edu
Part 1: Introduction to IR and MS Dallas K. Bates 2006
Table of Contents Problem 1 Molecular Formula/MW.page 2 Problem 2 Molecular Formula/MW...page 3 Hints for solving IR- and MS based spectroscopy problems.page 5 Guidelines for preparing your Bluebook of Useful Spectroscopic Information....page 7 IR spectra only Problem 3 .page 8 Problem 4 .page 12 Problem 5 .page 16 Mass spectra only Problem Problem Problem Problem Problem Problem Problem Problem Problem Problem Problem Problem 6 Exact Mass/Isotope ratios.page 19 7 predicting fragmentation..page 21 8 predicting fragmentation..page 22 9 predicting fragmentation..page 23 10 .....page 24 11 .....page 25 12 ...page 26 13 ...page 27 14 .page 28 15 .page 29 16 .page 30 17 .page 31
IR + MS problems Problem Problem Problem Problem Problem Problem Problem Problem Problem Problem 18 .page 32 19 .page 33 20 .page 37 21 .page 38 22 .page 39 23 .page 40 24 .page 41 25 .page 43 26. Using on-line IR databases page 45 27 IR+MS+1H NMR problem page 46
Problem 1 An article in the December 28, 2001 issue of the Journal of Organic Chemistry describes the isolation of a compound the authors named nomofungin by a bioassay-directed isolation procedure. The compound shows biological activity (microfilament disruption) analogous to Taxol, a drug used in cancer treatment. It was isolated from a fungus collected on the campus of the University of Hawaii at Manoa. As the culture was processed it stopped producing this compound and subsequent attempts to find more of the native fungus failed (hence nomofungin). (a) What is the molecular formula of nomofungin? ______________________________ (b) What is the molecular weight of nomofungin (round to ONE decimal place)? ____________ (c) At what nominal m/z value would you expect to see the molecular ion peak of nomofungin in a low resolution mass spectrum? ___________
Me N H O
N N O
NOMOFUNGIN
Problem 2 An article in the July 14, 2000 issue of the Journal of Organic Chemistry describes the isolation of compound 2 from human urine, its characterization by UV, 1H NMR, 13C NMR, low resolution mass spec (LRMS) with FAB volatilization of the sample (its mp is > 400 oC), HRMS, combustion microanalysis, and formal total synthesis.
(a) What is the molecular formula of 2? ______________________________ (b) What is the molecular weight of 2 (to one decimal place)? _____________ (c) At what m/z value would you expect to see the molecular ion peak of 2? __________
H N HO HO S
COOH
N H COOH 2
Some hints for solving problems
IR Problems
Initial analysis of an IR spectrum requires only a couple of minutes looking for the presence or absence diagnostic peaks for common functional groups. In many cases what is not seen in the spectrum is as important as what is seen. For example, it is possible to ascertain very quickly if a carbonyl group present or not present in an unknown sample. If present, with a little additional work it is usually possible to determine what type of carbonyl (amide, acid chloride, ester, ketone, conjugated or nonconjugated, etc.) the unknown sample contains. IR spectra are usually used in conjunction with other spectral data. The main use is to confirm suspicions raised by NMR or mass spec data about functional groups present or absent. For example, coupling constants and chemical shifts in a 1H NMR may point to the presence of a trans-alkene. Looking for peaks in the IR to differentiate cis- from trans- isomers would be useful to reinforce this initial hypothesis about the presence and stereochemistry of the double bond. Figure 1 IR spectrum of acetone. (note large C=O stretch at 1715 cm-1 and absence of any signals >3000 cm-1 (no OH, NH, alkene, or aryl CHs)
Mass Spectroscopy Problems

3. Determine the masses of the fragments lost to produce the major ions. What are you looking for are 2. To help identify the M+, look masses that equate with common for isotope clusters and apply the fragments lost, such as M-15 for nitrogen rule (is M+ even or the loss of methyl, M-35 for loss of odd?). Cl, etc. Figure 2 1. List M+ and the m/z values for all major fragment ions.
Bluebook of Useful Spectroscopic Information

You can purchase a bluebook from the bookstore and fill it with information you can use as a reference for solving problems in CH4412. You may also use it for all graded work (quizzes, tests, etc.). You may include material from any source, but you must hand-write any information in your bluebook. I would suggest you prepare four sections in your blue book dedicated to IR, MS, 1H NMR, and 13C NMR, respectively. It is a temptation to pack into your bluebook every detail about diagnostic spectroscopic information you can lay your hands on. However, I caution you to be selective. The more information, the longer it takes to find the specific information you need when you need it. If you have any questions about organizing material or what material would be most useful for your bluebook, just ask me.
Reiterating: ALL information in your bluebook must be hand-written by you.
page 7
Problem 3 Match the five IR spectra shown with the appropriate compound below. Indicate your answer by placing the spectrum number in the appropriate space. Note: spectra 1-3 are courtesy of Geetha Boreddy.
CN
IR Spectrum # ______
benzonitrile
cumene
CH3 C CH3 H
butanamine
NH2
NH2
2,4-dimethylaniline
CH3
CH3
N,N-diethylaniline
CH2CH3 N CH2CH3
Problem 3 Spectrum 1 (3354, 3290, 1611, 1477, 1330, 1176, 827, 688 cm-1)
Problem 3 Spectrum 2 (3065, 2229, 1598, 1491, 1447, 1288, 760, 688 cm-1)
Problem 3 Spectrum 3 (some major peaks: 2961, 1451, 1383, 760, 698 cm-1)
Problem 3 Spectrum 4 (some major peaks: 3473, 3383, 1622, 1477, 760 cm-1)
Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 5, 2004)
10
Problem 3 Spectrum 5 (2970, 1597, 1506, 1265, 1199, 744, 692 cm-1)
11
Problem 4 Seven IR spectra are shown below and on the following pages. Based on functional group information obtained from these spectra, answer the following questions by supplying the appropriate compound number (a compound may be used more than once or not at all; some questions may have more than one correct answer). (i) (ii) (iii) (iv) (v) Which compound contains an aromatic ring? Which compound would be reduced by NaBH4 (in EtOH/NaOH)? Which could be a reaction product from a NaBH4 reduction? Which is 2-methylpropanonitrile? Which is a primary (1o) amine?
Problem 4 Compound 1 (IR summary: 3348, 2960, 1426, 1368, 1164, 1139,
1116, 1067, 1017, 921, 827, 649 cm-1)
12
Problem 4 Compound 2 (some major absorptions: 2960, 1716, 1426, 1407,

1367, 1171, 594 cm-1)

1606, 1465, 1379, 837 cm-1)
13

1039, 1016, 904, 852 cm-1)
Problem 4 Compound 5 (some major peaks: 2986, 2246, 1476, 1460, 1392,
1372, 1323, 1173, 1106, 934, 916, 751, 545 cm-1)
14
Problem 4 Compound 6 (IR summary: 3046, 3035, 1481, 1430, 730, 700 cm-1)
Problem 4 Compound 7 (IR summary: 3077, 2970, 1651, 1466, 887 cm-1)
15
Problem 5 IR spectra (labeled A, B, C, and D) for four isomers (C5H10) appear on the next several pages. These compounds are 1-pentene, cis-2pentene, trans-2-pentene, and 2-methyl-1-butene. Complete the Table provided below match each compound to the appropriate spectrum and list the peaks that are useful for the assignments. Table Spectrum A B C D Compound Diagnostic bands (cm-1)
Note: the intensity of a band in an IR spectrum is proportional to the change in dipole moment during the molecular vibration. Consequently, some bands in nearly symmetrical compounds are quite weak. For example, the CC stretch in 2-butyne, which is symmetrical around the triple bond, does not appear in the spectrum; in 2-pentyne, the band is present but weak.
16
Spectrum A
100 90 80 % Transmittance 70
FTIR
NEAT
2844.5
1457.9
60 50 40 30
3079.8 1643.1 991.2
2875.3
910.2 2929.3
20
4500 4250 4000 3750 3500 3250
2962.1
3000
2750
2500
2250
2000
1750
1500
1250
1000
750
500
250
Wavenumbers (cm-1)
Sigma-Aldrich Co. ALL RIGHTS RESERVED
Spectrum B
FTIR
NEAT
100
90
1658.5 1373.1 1305.6 1403.9 933.4
80 % Transmittance
70
1456.0
60
2877.3 3016.1 2935.1
696.2
50
40
2966.0
30
4500 4250 4000 3750 3500 3250
3000
2750
2500
2250
2000
1750
1500
1250
1000
750
500
250
Wavenumbers (cm-1)
17
Spectrum C
FTIR
NEAT
100 90 80 % Transmittance 70 60
1440.6
1378.9
943.0 3023.8 1454.1 2856.1 2875.3
50 40 30 20
4500 4250 4000 3750 3500 3250
2921.6 964.2 2964.0
3000
2750
2500
2250
2000
1750
1500
1250
1000
750
500
250
Wavenumbers (cm-1)
Spectrum D
100 90 80 % Transmittance 70 60 50
FTIR
NEAT
1375.0
40 30 20
4500 4250 4000 3750 3500 3250
3075.9 2854.1
1650.8 1454.1 887.1
2917.8 2881.1 2937.1 2969.8
3000
2750
2500
2250
2000
1750
1500
1250
1000
750
500
250
Wavenumbers (cm-1)
18
Problem 6 Isotope peaks in LREI mass spectra can sometimes provide valuable information about the elemental composition of a compound. There are many computer programs available (some are available on the web as freeware) that will calculate expected ratio of P/P+1/P+2 (where P = a peak height) based on the elements present in the sample molecule and the isotopic abundances for those elements. The Table on the next page (from Spectrometric Identification of Organic Compounds, 4th edition, p. 46) lists possible formulae for an m/z 130 peak (P) in an EI mass spectrum. Also listed are the calculated P+1 and P+2 values (for compounds containing C, H, N, and O). The formulae appearing in this Table may be molecular ions or fragment ions, all having a nominal mass of 130. For example, note that the second item in the list is C3H4N3O3; we know from the Nitrogen Rule that this must be a fragment ion, not a molecular ion. Why? Because the Nitrogen Rule states that a molecular ion for a molecular formula containing an odd number of nitrogen atoms must be odd. Since 130 is an even number, this molecular formula can not represent a molecular ion it must represent a fragment ion. Two mass spectra are shown below. One is a MS of quinoxaline and the other is for phenylpropargylaldehyde (both nominal MW = 130). Based on the M/M+1/M+2 ratios in the respective mass spectra, determine the molecular formula for phenylpropargylaldehyde and quinoxaline. Then, based on your formula, determine the HDI of each compound. Phenylpropargylaldehyde
132 131 130 129 0.7 9.9 100 93.0
Quinoxaline
132 131 130 129 0.4 9.6 100 2.0
19
Problem 6. Predicted P+1: P+2 ratios for an m/z 130 peak. Nominal Mass = 130 C3H2N2O4 C3H4N3O3 C3H6N4O2 C4H4NO4 C4H6N2O3 C4H8N3O2 C4H10N4O C5H6O4 C5H8NO3 C5H10N2O2 C5H12N3O C5H14N4 C6H10O3 C6H12NO2 C6H14N2O C6H16N3 C6N3O C6H2N4 C7H14O2 C7H16NO C7NO2 C7H18N2 C7H2N2O C7H4N3 C8H18O C8H2O2 C8H4NO C8H6N2 C9H6O C9H8N C10H10 P+1* 4.19 4.57 4.94 4.92 5.30 5.67 6.05 5.66 6.03 6.40 6.78 7.15 6.76 7.14 7.51 7.88 7.67 8.04 7.87 8.24 8.02 8.62 8.40 8.77 8.97 8.75 9.13 9.50 9.86 10.23 10.97 P+2* 0.87 0.69 0.50 0.90 0.72 0.54 0.36 0.93 0.75 0.58 0.40 0.22 0.79 0.62 0.45 0.27 0.46 0.29 0.67 0.50 0.68 0.33 0.51 0.34 0.56 0.74 0.57 0.40 0.63 0.47 0.54 Exact Mass 130.0014 130.0253 130.0491 130.0140 130.0379 130.0617 130.0856 130.0266 130.0504 130.0743 130.0981 130.1220 130.0630 130.0868 130.1107 130.1346 130.0042 130.0280 130.0994 130.1233 130.9929 130.1471 130.0167 130.0406 130.1358 130.0054 130.0293 130.0532 130.0419 130.0657 130.0783
* Value when P has been normalized (scaled) to 100.
20
Problem 7 Draw the structures of two fragments expected to be produced in the LREIMS of compound 1.
CH3 1 O
Notes: LREIMS = Low Resolution Electron Impact Mass Spectrum Major fragments that appear in EIMS are often produced by cleavage of easily broken bonds in the molecule. One easy way to identify these easily broken bonds is to locate bonds that will form a stable carbocation (the other species from the bond cleavage will be a free radical) when they are broken. Recall from sophomore organic chemistry that benzyl and allyl carbocations are very stable, followed by tertiary carbocations (3o), secondary (2o), and the not so stable primary (1o). Benzyl and allyl carbocations derive their stability from pi electron delocation (resonance-stabilization). Some other common resonance-stabilized cations are acylium (a) and the ions (b) and (c) [oxonium and iminium ions, respectively].
Least stable
Most stable
CH2
CH3
CH2
(a) (b) (c)
21
Problem 8 Predict peaks expected in the LREIMS of benzyl acetate. List peaks in order of decreasing m/z: (random number of spaces provided) _____ ____ ____ ____ ____ ____ ____ ____ ____
22
Problem 9 Predict the LREIMS of 4-chloroacetophenone (the structure is shown in the box below).
List peaks in order of decreasing m/z.

O CH3 Cl
23
Problem 10 (A) Identify the m/z values for the base peak and molecular ion (M+) in the mass spectrum shown in Figure 1. Figure 1
(B)
Suggest a structure for the compound whose mass spectrum (LRMS) is shown in Figure 2. Also suggest a structure for m/z 77 and for the fragment lost from the M+ to form m/z 77. Figure 2
24
Problem 11 (A) (B) Identify the m/z values for the base peak and molecular ion (M+) in the mass spectrum shown Suggest a structure for the compound producing this spectrum. Also suggest a structure for m/z 91 and for the fragment lost from the M+ to form m/z 91.
25
Problem 12 Two LREIMS are shown below. Other than carbon and hydrogen atoms, each compound contains one oxygen atoms.
MS A m/z (rel abund): 50(12), 51(22), 77(52), 105(100), 140(4), 142(1.3)
MS B
43 (14), 75(17), 111(42/113(13.7), 139(100)/141(31.7), 154(26.7)/ 156(8.8)
Source: www.aist.go.jp/RIODB/SDBS (National Institute of Advanced Industrial Science and Technology, January 18, 2006).
26
Problem 13 The compound with EIMS shown below contains only C, H, and O. Identify the molecular ion and the base peak as well as any characteristic isotope clusters. Prepare a table of major fragment m/z values and the mass lost to form these fragments. Use these data to formulate a structure for this compound.
27
Problem 14 The compound with EIMS shown below contains only C, H, O and chlorine. Identify the molecular ion and the base peak as well as any characteristic isotope clusters. Prepare a table of major fragment m/z values and the mass lost to form these fragments. Use these data to formulate a structure for this compound.
28
Problem 15 The compound with EIMS shown below contains only C, H, and S. Identify the molecular ion and the base peak as well as any characteristic isotope clusters. Prepare a table of major fragment m/z values and the mass lost to form these fragments. Use these data to formulate a structure for this compound.
29
Problem 16 In addition to the element suggested by the molecular isotope cluster (out past m/z 220), the compound with EIMS shown below contains C, H, and O. Identify the molecular ion and the base peak. Prepare a table of major fragment m/z values and the mass lost to form these fragments. Use these data to formulate a structure for this compound.
30
Problem 17 The compound with EIMS shown below contains C, H, O and chlorine (C9H11ClO). Identify the molecular ion and the base peak. Prepare a table of major fragment m/z values and the mass lost to form these fragments. Use these data to formulate a structure for this compound.
31
Problem 18 Suggest a structure for compound 1 whose mass spectra (LREIMS) are provided. Amongst the atoms present are 9 carbon atoms and 1 oxygen atom. IR (KBr):1684 cm-1; LREIMS [m/z (rel int): (shown on spectrum) Compound1
(139(100)

111(39)
50(11)75(23)141(32) 113(12) 168(16.5) 170(5.4)
32
Problem 19 IR and mass spectra for three compounds (C9H10O) whose structures are shown below are given on the following pages. Answer the three questions below about the structures and spectra. (A) For the three structures shown, predict differences expected to be observed in the IR spectra. (B) For each of the three structures shown, predict the structure and m/z values for major fragments. It would be useful to make a table containing the structures and their m/z values. (C) Examine the IR spectra for the three compounds. What initial conclusions about which structure corresponds to each spectrum can you make? (D) Examine each mass spectrum provided. Based on your table of expected fragments for each structure, assign a mass spectrum to each structure. Do these assignments agree with the preliminary conclusions reached from examining the IR spectra?
CH3 O O X Y H
The spectra for this problem are from the NIST database.
33
Problem 19 Compound 1
IR spectrum (gas phase major peaks: 1705, 1218 cm-1)
Mass spectrum (major peaks: m/z 134, 105, 77, 51)
34
IR spectrum (gas phase some major peaks: 3078, 3038, 2966, 2930, 1730 cm-1)
Mass spectrum (major peaks: m/z 134, 91, 65, 63, 51, 43, 39)
35
IR spectrum (gas phase major peaks: 2808, 2710, 1744 cm-1)
Mass spectrum (major peaks: m/z 134, 105, 91, 79, 77, 51, 39)
36
Problem 20 The IR (liquid film) and mass spectrum (LREI) of a benzoic acid derivative prepared as an intermediate in a multi-step chemical synthesis are shown below. Place your answers to the following four questions in the appropriate space on the attached sheet. (A) Suggest a structure consistent with these data. (B) Assign the absorption at 1791 cm-1 in the IR spectrum. (C) What do the peaks at m/z 170/168 indicate? (D) Assign a structure to the peaks at m/z 133 and 105.
IR summary: 1791, 1467, 1186, 851, 774, 754, 711 cm-1.
MS summary [m/z (relative intensity)]: 170 (1.13) 168 (3.91) 133 (100) 105 (60)
Spectra courtesy of Geetha Boreddy
37
Problem 21 Based upon the IR and mass spectral data shown below, match spectra X, Y, Z to compounds A, B, and C.
38
Problem 22 The IR (film) and mass spectrum (LREI) of an unknown compound are shown below. Note: An apparent contaminant shows peaks at 3642 and 3549 cm-1 (what functional group accounts for this?). (A) Suggest a structure consistent with these data. (B) Identify the functional group responsible for the absorptions at 2246, 1392 and 1372 cm-1. (C) Suggest structures for the M-1, M-15 and M-27 peaks.
IR summary: 2986, 2246, 1460, 1392, 1372, 1323, 1173, 1106, 934, 916 cm-1)
Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 9, 2004) MS summary: m/z 69, 68 (M-1), 54, 42.
39
Problem 23 The IR (KBr pellet) and mass spectrum (LREI) of an unknown compound are shown below. (A) Suggest a structure for the compound. (B) Propose a mechanism for formation of the m/z 44 and m/z 59 peaks by cleavages in the molecular ion.
IR summary: 3366, 3184, 2962, 1662, 1634, 1430, 1418, 1379, 1344, 1313, 1263, 1145, 713, 666 cm-1
Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 12, 2004) MS peak listing:
87 86 72 59 44 43 42 41 39 29 27
2 3 19 100 66 32 7 53 11 26 26
40
Problem 24 The following IR and mass spectra are for two isomeric compounds (compounds A and B). The mass spectra are quite different, but they exhibit similar IR spectra. Propose structures for compounds A and B.
IR summary: (broad peak >3000 cm-1 = impurity, 3051, 2801, 2230, 1689, 1403, 1367, 1266, 833 cm-1.
Compound A
Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 12, 2004) Mass spectrum line listing:
145 130 102 75 43
17 100 47 10 18
41
Problem 24 (Data for Compound B)

IR summary: (broad peak >3000 cm-1 = impurity, 3072, 2955, 2924, 2224 (CN), 1689, 1220, 767 cm-1.
Mass spectrum line listing: 145 105 77 51 50 4 100 59 21 7
42
Problem 25 The IR and mass spectra of two isomeric compounds (A and B) are shown below. Suggest a structure for each compound. Compound A
Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 12, 2004) Mass spectrum line listing: 142 141 140 105 77 51 39 6 2 20 100 11 6 4
43
Problem 25 (Data for compound B)
Mass spectrum line listing 142 141 140 105 91 77 65 51 39 4 1 14 3 100 6 5 7 3
44
Problem 26
Using on-line Chemistry Databases
In this exercise you will use the National Institute of Standards and Technology (NIST) on-line Chemistry WebBook and the SDBS Integrated Spectral Data Base System for Organic Compounds to find the MS and IR of an assigned organic compound, analyze the spectra to assign structures to the important fragments and functional groups to representative bands in the respective spectra. The NIST Chemistry WebBook contains thermochemical, heat of reaction data, and IR and MS data. The SDBS Integrated Spectral Data Base System for Organic Compounds contains IR, MS, 1H and 13C NMR spectra. The databases may be searched by name, chemical formula, CAS registry number, molecular weight, or user specified properties. The URLs are: http://webbook.nist.gov and http://www.aist.go.jp/RIODB/SDBS
Specific Assignment:
Your assigned compound will be announced in class. A sample report is also posted on the CH4412 web page. Search for the IR and mass spectrum for your assigned compound. Report the following on a sheet of paper to be handed-in by the date specified on the bulletin board: (A) The name and structure of the compound (and CAS registry number, if available). (B) Mass spectrum, IR spectrum, or both depending upon availability in the database. (C) Structures of fragment ions (mass spec) and functional group absorptions (IR). This assignment will be handed in and graded as a quiz (10 points).
NOTE: To print the MS and IR spectra for your compound, you need to select the large spectrum image (click on the icon just below the spectrum). You will also need to change the print orientation from portrait to landscape (in the print window click the properties button next to the printer name to get the appropriate text box). For the IR spectrum, you may need to choose Reverse X to present the spectrum in the standard presentation format having wave numbers (cm-1) decrease from left to right in the spectrum - this will make more sense when you look at a spectrum.
45
Problem 27
The attached IR, LRMS, and 1H NMR were obtained for a compound C12H16O. Propose a structure for the compound producing these spectra and assign signals to the structure.
46
Problem 27 (continued)
H NMR spectrum
47
Problem 27 (continued) LREI Mass Spectrum
48

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Spectroscopy Problems Part 1 Introduction to IR and Mass Spectroscopy

Dallas K. Bates Michigan Technological University

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Some hints for solving problems

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Mass Spectroscopy Problems

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Bluebook of Useful Spectroscopic Information

Reiterating: ALL information in your bluebook must be hand-written by you.

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 5, 2004)

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 5, 2004)

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Problem 4 Compound 2 (some major absorptions: 2960, 1716, 1426, 1407,

Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 5, 2004)

Problem 4 Compound 3 (some major absorptions: 3369, 3293, 2960, 2928,

Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 5, 2004)

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Problem 4 Compound 4 (some major absorptions: 2928, 2853, 1460, 1257,

Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 5, 2004)

1372, 1323, 1173, 1106, 934, 916, 751, 545 cm-1)

Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 5, 2004)

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 9, 2004)

Source: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (February 9, 2004)

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

3079.8 1643.1 991.2

Part 1: Introduction to IR and MS Dallas K. Bates 2006

943.0 3023.8 1454.1 2856.1 2875.3

2921.6 964.2 2964.0

1650.8 1454.1 887.1

2917.8 2881.1 2937.1 2969.8

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

* Value when P has been normalized (scaled) to 100.

Part 1: Introduction to IR and MS Dallas K. Bates 2006

(a) (b) (c)

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

List peaks in order of decreasing m/z.

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

43 (14), 75(17), 111(42/113(13.7), 139(100)/141(31.7), 154(26.7)/ 156(8.8)

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

Part 1: Introduction to IR and MS Dallas K. Bates 2006

50(11)75(23)141(32) 113(12) 168(16.5) 170(5.4)

Part 1: Introduction to IR and MS Dallas K. Bates 2006