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Chapter 14
NMR Spectroscopy

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14-00CO
Title
 1-Nitropropane
Caption
 Ball-and-stick model and 1H NMR spectrum of 1-nitropropane.
Notes
 NMR spectroscopy is the single most useful tool for elucidating the structures of organic compounds.
Keywords
 1-nitropropane, ball-and-stick, NMR
14-01
Title
 Figure 14.1
Caption
 Nuclear spins in a magnetic field.
Notes
 In the absence of an applied magnetic field nuclei do not align their nuclear spins. In an applied magnetic field nuclei orient their nuclear spins either parallel or antiparallel to the applied field. The parallel orientation is more stable.
Keywords
 figure, 14.1, nuclear, spins, magnetic, field
14-02
Title
 Figure 14.2
Caption
 Energy vs. field strength.
Notes
 The energy difference between the parallel orientation of a nuclear spin in a magnetic field and the antiparallel orientation of the spin in the field is proportional to the strength of the applied magnetic field.
Keywords
 figure, 14.2, energy, field, strength
14-03
Title
 Figure 14.3
Caption
 Schematic diagram of an NMR spectrometer.
Notes
 An NMR spectrometer is an instrument which measures the applied magnetic field strengths required to produce a certain energy difference between nuclear spins of various atoms in a molecule oriented parallel and antiparallel to the applied magnetic field. This information is used by chemists to help elucidate the structure of molecules of organic compounds.
Keywords
 figure, 14.3, schematic, diagram, NMR, spectrometer
14-04
Title
 Figure 14.4
Caption
 Shielding and resonance.
Notes
 Shielded nuclei come into resonance at lower frequencies than deshielded nuclei.
Keywords
 figure, 14.4, shielded, shielding, resonance, nuclei
14-05
Title
 Figure 14.5
Caption
 Proton NMR spectrum of 1-bromo-2,2-dimethylpropane.
Notes
 The methylene protons are much more deshielded than the methyl protons because they are closer to the electron-withdrawing bromine atom in a 1-bromo-2,2-dimethylpropane molecule.
Keywords
 figure, 14.5, NMR, bromodimethylpropane
14-05-00UN
Title
 Chemical Shifts
Caption
 Relationship between chemical shifts, electronic environments, and resonance frequencies for proton spins.
Notes
 Deshielded protons are protons in electron-poor environments. They sense strong applied magnetic fields and require high frequencies of rf to match the energy difference between their parallel and antiparallel spin states and cause resonance. They require lower applied magnetic field strengths to cause their parallel and antiparallel spin state energy differences to match the energy of a certain rf frequency, so they come into resonance "downfield." Shielded protons have the opposite properties of deshielded protons.
Keywords
 chemical, shifts, resonance, frequencies, shielding, deshielding
14-06
Title
 Figure 14.6
Caption
 Proton NMR spectra associated with Problem 10.
Notes
 The first spectrum is of iodopropane and the second is of chloropropane. Note that the methylene protons on the carbon bearing the halogen are more deshielded in the second spectrum than in the first due to the fact that chlorine is more electronegative than iodine.
Keywords
 figure, 14.5, problem, 10, iodopropane, chloropropane
14-07
Title
 Figure 14.7
Caption
 Proton NMR spectrum of 1-bromo-2,2-dimethylpropane showing proton integration line.
Notes
 The change in the height of the integration line is proportional to the number of protons causing the resonance line associated with the rise in the height of the integration line.
Keywords
 figure, 14.7, integration, bromodimethylpropane
14-08
Title
 Figure 14.8
Caption
 Proton NMR spetrum for Problem 15.
Notes
 The compound giving this spectrum is para-xylene. From Table 14.1 note that the chemical shift for a methyl group attached to a benzene ring is 2.3 ppm.
Keywords
 figure, 14.8, Problem, 15, para-xylene
14-09
Title
 Figure 14.9
Caption
 Induced magnetic fields created by pi electron response to applied magnetic fields.
Notes
 Pi electrons in aromatics and alkenes respond to applied magnetic fields by circulating in such a way as to create induced magnetic fields which are parallel to the applied magnetic fields around molecules of these substances and antiparallel to applied fields through the centers of these molecules.
Keywords
 figure, 14.9, induced, magnetic, fields, pi, electrons
14-10
Title
 Figure 14.10
Caption
 Proton NMR spectrum of 1,1-dichloroethane.
Notes
 The methyl proton signal is split into a doublet and the methine signal is split into a quartet by spin–spin coupling.
Keywords
 figure, 14.10, NMR, spectrum, dichloroethane
14-11
Title
 Figure 14.11
Caption
 Splitting of methyl proton signal of 1,1-dichloroethane.
Notes
 The signal for the methyl protons of 1,1-dichloroethane is split into a doublet by the methine proton.
Keywords
 figure, 14.11, methyl, protons, dichloroethane
14-12
Title
 Figure 14.12
Caption
 Splitting of methine proton signal of 1,1-dichloroethane.
Notes
 The signal for the methine proton of 1,1-dichloroethane is split into a quartet by the methyl protons.
Keywords
 figure, 14.12, sgnal, methine, proton, dichloroethane
14-13
Title
 Figure 14.13
Caption
 Magnetic alignment possibilities for three protons.
Notes
 Three protons can orient their spins in such a way that all three spins produce fields which are parallel to the applied field, two are parallel and one antiparallel to the applied field, one is parallel and two antiparallel, or all three spins oppose the applied field. There is only one possibility for the first and last of these options, but there are three possibilities for the second and third of these options.
Keywords
 figure, 14.13, magnetic, alignment, three, protons
14-14
Title
 Figure 14.14
Caption
 Proton NMR spectra for in-chapter Problem 18.
Notes
 The first spectrum is of 2-chloropropanoic acid and the second is of 3-chloropropanoic acid. The first spectrum shows a deshielded methine proton signal split into a quartet by three methyl protons and a shielded methyl proton signal split into a doublet by one methine proton. The second spectrum shows two sets of methylene proton signals split into triplets caused by pairs of methylene protons splitting each other's signals.
Keywords
 figure, 14.14, NMR, problem, 18
14-15
Title
 Figure 14.15
Caption
 Proton NMR spectrum of 1,3-dibromopropane.
Notes
 The signal for each pair of methylene protons on a carbon bearing a bromine is split by the two central protons into a triplet. These two triplets superimpose on each other, creating a single triplet for all of the deshielded hydrogens because all of these hydrogens are in an identical magnetic environment. The signal for the central methylene protons is split into a pentuplet by the four surrounding methylene protons.
Keywords
 figure, 14.15, NMR, dibromopropane
14-16
Title
 Figure 14.16
Caption
 Proton NMR spectrum of isopropyl butanoate.
Notes
 Splitting of signals by neighboring protons leads to, in order of increasing deshielding, a triplet, a doublet, a theroretical 12-line multiplet which shows less than 12 lines due to overlapping, a triplet, and a septuplet.
Keywords
 figure, 14.16, NMR, isopropyl, butanoate
14-17
Title
 Figure 14.17
Caption
 Proton NMR spectrum of 3-bromo-1-propene.
Notes
 Splitting of signals by neighboring protons leads to, in order of increasing deshielding, a doublet, two theoretical doublets of doublets, and a theoretical 12-line pattern. The protons labeled a and b should split each other's signals, but the splitting is too small to be observable in the spectrum in the figure, so the two theoretical doublets of doublets actually appear as simple doublets. The theoretical 12-line multiplet predicted for proton d shows less than 12 lines partly because protons b and c are indistinguishable by the NMR spectrometer used to generate the spectrum. The 9-line pattern which should result from protons b and c being indistinguishable is not seen either because some of these lines overlap each other.
Keywords
 figure, 14.17, NMR, 3-bromo-1-propene
14-17-01UN
Title
 A Quartet and a Doublet of Doublets
Caption
 Schematic depiction of the difference between a quartet and a doublet of doublets.
Notes
 Both a quartet and a doublet of doublets show four lines but the doublet of doublets shows the same intensity for all four lines, whereas the quartet shows lines with relative intensities of 1:3:3:1. The lines in a quartet must be equally spaced apart, whereas the lines in a doublet of doublets need not be equally spaced apart. Occasionally two of the lines of a doublet of doublets will overlap and give the appearance of a triplet with relative intensities of 1:2:1.
Keywords
 quartet, doublet, doublets
14-18
Title
 Figure 14.18
Caption
 Proton NMR spectrum of ethylbenzene.
Notes
 The ethyl group shows a shielded triplet and a deshielded quartet and the different kinds of aromatic protons all split each other's signals and pack the resulting lines into the same chemical shift area, resulting in a complex pattern. In practice the splitting between protons meta and para to one another is often too small to be observable with low- or medium-field NMR spectrometers.
Keywords
 figure, 14.18, NMR, ethylbenzene
14-19
Title
 Figure 14.19
Caption
 Proton NMR spectrum of nitrobenzene.
Notes
 The nitro group is powerfully electron withdrawing and its proximity to the various chemically different protons separates the signals of these protons from one another enough to see their signal multiplicities. The spectrometer used to generate this spectrum is not powerful enough to show mutual splitting of signals generated by protons substituted meta and para to one another, so the resulting spectrum is fairly simple. In order of increasing chemical shift a doublet of doublets followed by a triplet followed by a doublet is observed. These multiplets don't show the exact calculated relative intensities because multiplets generated by low- and medium-field instruments are asymmetric. As NMR field strengths increase the relative intensities of peaks in multiplets approaches theoretical values.
Keywords
 figure, 14.19, nitrobenzene, NMR
14-19-02P23
Title
 Problem 23
Caption
 Three proton NMR spectra corresponding to the molecular formulas and spectra given in in-chapter Problem 23.
Notes
 Compound a is propylbenzene, Compound b is 3-pentanone, and Compound c is ethyl benzoate.
Keywords
 problem, 23, propylbenzene, 3-pentanone, ethyl, benzoate
14-22
Title
 Figure 14.22
Caption
 Proton NMR and IR spectra of a compound with the molecular formula C9H10O described in Problem-Solving Strategy.
Notes
 From the molecular formula the compound has five units of unsaturation (rings and/or pi bonds). From the NMR four of these units are due to the presence of a benzene ring (peaks between 7 and 8 ppm). From the IR the other unit is a carbonyl (band at 1670 cm–1). The position of the carbonyl band shows that the carbonyl is in resonance with the aromatic ring. The shielded triplet and deshielded quartet in the NMR is characteristic of an ethyl group. The integration line in the NMR shows five aromatic protons, meaning that the ethyl group cannot be attached to the benzene ring. The conclusion from these considerations is that the compound is ethyl phenyl ketone.
Keywords
 figure, 14.22, problem-solving, NMR, IR
14-23
Title
 Figure 14.23
Caption
 Proton NMR and IR spectra of a compound with the molecular formula C8H10O described in in-chapter Problem 28.
Notes
 The molecular formula suggests four units of unsaturation, and the NMR spectrum shows that these can be accounted for by the presence of a benzene ring (lines near 7 ppm). The aromatic region shows two doublets, characteristic of a para-disubstituted aromatic compound. No O–H stretch is seen in the 3300–3400 cm–1 region of the IR, and a C–O stretch is seen at 1100 cm–1, suggesting an ether. The integration line in the NMR passes over two singlet signals, showing each signal to be caused by three protons, suggesting two methyl groups. One methyl group is in the right position to be attached to the benzene ring and the other is in the right position to be attached to an ether oxygen. The compound generating these spectra is para-methoxytoluene.
Keywords
 figure, 14.23, problem, 28, NMR, IR
14-24
Title
 Figure 14.24
Caption
 Splitting diagram for a doublet of doublets.
Notes
 This diagram shows how the signal from a proton split by two protons in different chemical environments should wind up split into four lines with equal intensities, which are not necessarily spaced apart equally.
Keywords
 figure, 14.24, splitting, diagram, doublets
14-25
Title
 Figure 14.25
Caption
 Splitting diagram for a quartet of triplets.
Notes
 This diagram shows how the signal from protons split by two protons in one chemical environment and three protons in a different chemical environment leads to a maximum of twelve lines. Fewer than twelve lines can be seen if some of the lines overlap. The exact number of lines observed depends on the values of the coupling constants associated with the signal splittings.
Keywords
 figure, 14.25, splitting, diagram, quartet, triplets
14-26
Title
 Figure 14.26
Caption
 Proton NMR spectrum of 1-chloro-3-iodopropane.
Notes
 The signal for the proton labeled "a" should give a maximum of 3 x 3 = 9 lines. Because the two signal-splitting coupling constants for these protons are nearly identical, only five lines are observed. In general when different protons mutually split the signals of a neighboring set of protons with similar coupling constants, the observed multiplet for the neighboring set of protons appears the same as if all of the signal-splitting protons were in an identical magnetic environment. In the example in the figure two pairs of protons in different magnetic environments act together to split the signal from a mutual neighbor into five lines, as if all four protons in the two pairs were in an identical magnetic environment.
Keywords
 figure, 14.26, NMR, 1-chloro-3-iodopropane
14-27
Title
 Figure 14.27
Caption
 Proton NMR spectra of cyclohexane-d11 at various temperatures.
Notes
 At higher temperatures molecular conformations change at speeds faster than the time scale of the spectrometer, and one signal is seen for each chemically distinct proton regardless of how many different magnetic environments it finds itself in due to conformation changes. Signal properties (multiplicities, intensities, etc.) are a population-weighted average of the properties of the signals arising from proton(s) from different conformers. At lower temperatures interconversion of conformers slows down, and eventually becomes slower than the time scale of the spectrometer. When this occurs each magnetically distinct proton in each conformer gives its own signal.
Keywords
 figure, 14.27, temperature, NMR, cyclohexane-d11
14-28a,b
Title
 Figure 14.28
Caption
 Proton NMR spectrum of pure ethanol (a) and ethanol contaminated with a trace of acid (b).
Notes
 In pure ethanol the alcohol hydrogen exchanges slowly enough that it couples with the adjacent methylene protons. If an alcohol is contaminated with a catalytic amount of acid the exchange speeds up to the point where the methylene protons show only an average interaction with the alcohol proton in various environments, and the alcohol proton likewise gives a signal corresponding to its average environment. No signal splitting is observed between an alcohol proton and neighboring protons in this circumstance.
Keywords
 figure, 14.28, NMR, ethanol, pure, contaminated, acid
14-29
Title
 Figure 14.29
Caption
 Proton NMR spectrum for in-chapter Problem 34.
Notes
 The molecular formula suggests 1 unit of unsaturation and the NMR shows a shielded triplet and an unshielded quartet consistent with an ethyl group with the quartet in the correct location for the methylene protons to be adjacent to a carbonyl group. The integration line shows two protons in the correct region to be amide hydrogens, suggesting that the compound generating the NMR spectrum is propanamide.
Keywords
 figure, 14.29, problem, 34, propanamide
14-30a,b
Title
 Figure 14.30
Caption
 Proton NMR spectra of 2-sec-butylphenol using, (a) a 60-MHz spectrometer, and (b) a 300-MHz spectrometer.
Notes
 Higher-field higher-frequency instruments separate proton signals more than lower-frequency instruments on an absolute basis but not on a relative (ppm) basis. Coupling constants do not change on an absolute basis, but decrease on a ppm basis on higher-frequency instruments. Thus, higher frequency instruments increase signal separation relative to signal splitting, yielding cleaner, less-overlapping signals. Generally for optimum resolution it is best to have the frequency differences of signal separation be at least ten times the frequency diferences of signal splitting (coupling constants).
Keywords
 figure, 14.30, 2-sec-butylphenol, resolution, field, strength
14-31
Title
 Figure 14.31
Caption
 The splitting pattern of an ethyl group as a function of the Dn/J ratio.
Notes
 When the coupling constant for splitting of a signal equals the separation between signals, everything coalesces into a single peak. When the separation between signals is at least five times the coupling constant for splitting of signals, an ethyl group is clearly presented by an NMR spectrometer. Other more complex sets of lines require higher Dn/J ratios.
Keywords
 figure, 14.31, splitting, pattern, ethyl, Dn/J
14-32
Title
 Figure 14.32
Caption
 Proton-decoupled carbon-13 NMR spectrum of 2-butanol.
Notes
 When protons are decoupled from carbon-13 resonances spin–spin splitting between carbons and attached protons does not occur, so each carbon in a unique magnetic environment produces a singlet. The relative frequencies (in ppm) of carbons in various chemical environments are found in Table 14.4. 2-Butanol has carbons in four different environments, so it produces four singlets at frequencies consistent with values found in Table 14.4.
Keywords
 figure, 14.32, proton-decoupled, carbon-13, NMR, 2-butanol
14-33
Title
 Figure 14.33
Caption
 Proton-coupled carbon-13 NMR spectrum of 2-butanol.
Notes
 When the proton decoupler in a carbon-13 NMR is switched off, a proton-coupled spectrum is produced. Carbon-13 atoms which produce signals split the signals into one more line than the number of attached hydrogens. Thus, a proton-coupled spectrum can be used to determine how many protons are attached to the carbons producing each signal.
Keywords
 figure, 14.33, proton-coupled, carbon-13, NMR, 2-butanol
14-34-07UN
Title
 Problem-Solving Strategy Carbon-13 NMR Spectrum
Caption
 Proton-decoupled carbon-13 NMR spectrum of a compound with a molecular formula of C9H10O2.
Notes
 The molecular formula suggests five units of unsaturation. The peaks in the 126–134 ppm range appear to be aromatic carbons from their chemical shifts and proximity to one another. This accounts for four units of unsaturation. The fifth unit of unsaturation appears to be an ester carbonyl group from the position of the peak at 166 ppm. The peaks at 15 ppm and 61 ppm appear to be positioned correctly to suggest an ethyl group attached to an oxygen. Piecing this information together suggests ethyl benzoate as the compound generating the spectrum.
Keywords
 problem-solving, C9H10O2, carbon-13
14-35
Title
 Figure 14.35
Caption
 Identify the compounds generating the NMR spectra in Problem 14.35. The first spectrum is a proton-decoupled carbon-13 spectrum of a compound with the molecular formula C11H22O. The second spectrum is a proton-decoupled carbon-13 spectrum of a compound with the molecular formula C8H9Br. The third spectrum is a proton spectrum of a compound with the molecular formula C6H10O. The last spectrum is a proton-decoupled carbon-13 spectrum of a compound with the molecular formula C6H12.
Notes
 The first spectrum is 6-undecnone, the second spectrum is 1-bromo-2-phenylethane, the third spectrum is cyclohexanone, and the fourth spectrum is 3-hexene.
Keywords
 figure, 14.35, 1-bromo-2-phenylethane, cyclohexanone, 3-hexene
14-35-01P38
Title
 Figure 14.35
Caption
 Identify the compounds generating the NMR spectra in Problem 14.35. The first spectrum is a proton-decoupled carbon-13 spectrum of a compound with the molecular formula C11H22O. The second spectrum is a proton-decoupled carbon-13 spectrum of a compound with the molecular formula C8H9Br. The third spectrum is a proton spectrum of a compound with the molecular formula C6H10O. The last spectrum is a proton-decoupled carbon-13 spectrum of a compound with the molecular formula C6H12.
Notes
 The first spectrum is 6-undecnone, the second spectrum is 1-bromo-2-phenylethane, the third spectrum is cyclohexanone, and the fourth spectrum is 3-hexene.
Keywords
 figure, 14.35, 1-bromo-2-phenylethane, cyclohexanone, 3-hexene
14-36
Title
 Figure 14.36
Caption
 DEPT carbon-13 NMR spectrum of citronellal.
Notes
 The DEPT technique can be used to show only methyl, only methylene, or only methine carbons.
Keywords
 figure, 14.36, DEPT, citronellal
14-37a,b
Title
 Figure 14.37
Caption
 COSY spectra of ethyl vinyl ether (a) shows a stack plot and (b) shows a contour plot.
Notes
 In the contour plot locations of correlation peaks (A, B, and C) correspond to coupling between hydrogens generating peaks on the diagonal axis. Correlation peak "A" is generated by interaction of "a" protons with "b" protons. Correlation peak "B" is generated by interaction of "c" protons with "e" protons. Correlation peak "C" is generated by interaction of "d" protons with "e" protons.
Keywords
 figure, 14.23, COSY, ethyl, vinyl, ether
14-38
Title
 Figure 14.38
Caption
 COSY spectrum of 1-nitropropane.
Notes
 "A" shows that "a" is coupled to "b" and "B" shows that "b" is coupled to "c."
Keywords
 figure, 14.38, COSY, 1-nitropropane
14-39
Title
 Figure 14.39
Caption
 COSY spectrum for in-chapter Problem 39.
Notes
 Identify pairs of coupled protons in 2-methyl-3-pentanone using the COSY spectrum in Figure 14.39. Protons "c" and "a" are coupled and protons "b" and "d" are coupled.
Keywords
 figure, 14.39, COSY, problem, 39, 2-methyl-3-pentanone
14-40
Title
 Figure 14.40
Caption
 HETCOR spectrum of 2-methyl-3-pentanone.
Notes
 A HETCOR spectrum shows the correlation between carbons in a carbon-13 spectrum and protons in a proton spectrum. Protons which correlate with carbons are bonded to the carbons they correlate with. In 2-methyl-3-pentanone the most upfield protons are bonded to the most upfield carbon, the next-most upfield protons are bonded to the next-most upfield carbon, etc.
Keywords
 figure, 14.40, HETCOR, 2-methyl-3-pentanone
14-41-13P43a-c
Title
 End-of-Chapter Problem 43
Caption
 Proton NMR spectra associated with end-of-chapter Problem 43.
Notes
 Match the proton NMR spectra with compounds whose structural formulas are shown in Problem 43.
Keywords
 end-of-chapter, problem, 43
14-41-21P47a-c
Title
 End-of-Chapter Problem 47
Caption
 Proton NMR spectra associated with end-of-chapter Problem 47.
Notes
 The proton NMR spectra of three isomers with the molecular formula C4H9Br are displayed in the figure. Figure out from the spectra which isomer corresponds to each spectrum.
Keywords
 end-of-chapter, problem, 47
14-41-22P49
Title
 End-of-Chapter Problem 49
Caption
 Spin-coupled carbon-13 NMR spectrum associated with end-of-chapter Problem 49.
Notes
 The NMR spectrum shown is of a compound with the molecular formula C&H14O. Determine the structure of this compound from the spectrum.
Keywords
 end-of-chapter, problem, 49
14-41-23P51a-c
Title
 End-of-Chapter Problem 51
Caption
 Proton NMR spectra associated with end-of-chapter Problem 51.
Notes
 The proton NMR spectra of three isomers with the molecular formula C7H14O are displayed in the figure. Figure out from the spectra which isomer corresponds to each spectrum.
Keywords
 end-of-chapter, problem, 51
14-41-24P53a
Title
 End-of-Chapter Problem 53a
Caption
 IR and proton NMR spectra associated with end-of-chapter Problem 53a.
Notes
 Determine the structure of the compound which generates the IR and NMR spectra shown and has the molecular formula shown above the IR spectrum.
Keywords
 end-of-chapter, problem, 53a
14-41-25P53b
Title
 End-of-Chapter Problem 53b
Caption
 IR and proton NMR spectra associated with end-of-chapter Problem 53b.
Notes
 Determine the structure of the compound which generates the IR and NMR spectra shown and has the molecular formula shown above the IR spectrum.
Keywords
 end-of-chapter, problem, 53b
14-41-26P53
Title
 End-of-Chapter Problem 53c
Caption
 IR and proton NMR spectra associated with end-of-chapter Problem 53c.
Notes
 Determine the structure of the compound which generates the IR and NMR spectra shown and has the molecular formula shown above the IR spectrum.
Keywords
 end-of-chapter, problem, 53c
14-41-27P53d
Title
 End-of-Chapter Problem 53d
Caption
 IR and proton NMR spectra associated with end-of-chapter Problem 53d.
Notes
 Determine the structure of the compound which generates the IR and NMR spectra shown and has the molecular formula shown above the IR spectrum.
Keywords
 end-of-chapter, problem, 53d
14-41-29P55
Title
 End-of-Chapter Problem 55
Caption
 Proton NMR spectrum associated with end-of-chapter Problem 55.
Notes
 An alkyl halide reacts with an alkoxide ion to yield the substance which gives the proton NMR spectrum shown in the figure. Determine the identities of the alkyl halide and the alkoxide ion.
Keywords
 end-of-chapter, problem, 55
14-41-30P56a,b
Title
 End-of-Chapter Problem 56
Caption
 Proton NMR spectra associated with end-of-chapter Problem 56.
Notes
 Determine the structures of the two compounds which generate the proton NMR spectra shown using the molecular formulas given.
Keywords
 end-of-chapter, problem, 56
14-41-31P57
Title
 End-of-Chapter Problem 57
Caption
 Proton NMR spectrum associated with end-of-chapter Problem 57.
Notes
 Determine which protons in 2-propen-1-ol give rise to each of the signals observed in the proton NMR spectrum of this compound, shown in the figure.
Keywords
 end-of-chapter, problem, 57, 2-propen-1-ol
14-41-33P59a,b
Title
 End-of-Chapter Problem 59
Caption
 Proton NMR spectra associated with end-of-chapter Problem 59.
Notes
 The proton NMR spectra of two isomers with the molecular formula C11H16 are displayed in the figure. Figure out from the spectra which isomer corresponds to each spectrum.
Keywords
 end-of-chapter, problem, 59
14-41-35P63a,b
Title
 End-of-Chapter Problem 63
Caption
 Proton NMR spectra associated with end-of-chapter Problem 63.
Notes
 Determine the structures of the four compounds which generate the proton NMR spectra shown in the figure using the molecular formulas given.
Keywords
 end-of-chapter, problem, 63
14-41-36P63
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