Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition

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Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 1 preview image

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Answers for Student Exercises 1.1 to 1.51Atom Type# of AtomsMassTotal MassHydrogen221.0078322.17226Carbon1012.00000120.00000Nitrogen014.00310.00000Oxygen015.99490.00000Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =0142.17226Exact Massa3-ethyloctaneC10H22- (C2H5)Rule 3- (C5H11)Rule 3- (CH2=CH2)Rule 9Hor- (C4H9)Rule 5 and 6- (CH2=CH2)Rule 6- (C3H7)Rule 3Atom Type# of AtomsMassTotal MassHydrogen181.0078318.14094Carbon1012.00000120.00000Nitrogen014.00310.00000Oxygen015.99490.00000Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =2138.14094Exact Massb3-butylcyclohex-1-eneC10H18

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Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 3 preview image

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Answers for Student Exercises 1.1 to 1.52Atom Type# of AtomsMassTotal MassHydrogen221.0078322.17226Carbon1112.00000132.00000Nitrogen014.00310.00000Oxygen015.99490.00000Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =1154.17226Exact Massd(E)-undec-3-eneC11H22or- (CH3)Rule 5- (C6H13)Rule 5H- (C7H14)Rule 9Atom Type# of AtomsMassTotal MassHydrogen181.0078318.14094Carbon1312.00000156.00000Nitrogen014.00310.00000Oxygen115.994915.99490Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =5190.13584Exact MassOc2-methyl-1-phenylhexan-1-oneC13H18OO- (C6H13)Rule 8OOO- (C6H5)Rule 8OOH- (C4H8)Rule 9OHOHO- (CO)Rule 8+9

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 4 preview image

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Answers for Student Exercises 1.1 to 1.53Atom Type# of AtomsMassTotal MassHydrogen181.0078318.14094Carbon1212.00000144.00000Nitrogen014.00310.00000Oxygen015.99490.00000Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =4162.14094Exact Masse1-(hexan-2-yl)benzeneC12H18- (CH3)Rule 7- (C4H9)Rule 7- (C4H8)Rule 9HHHAtom Type# of AtomsMassTotal MassHydrogen161.0078316.12528Carbon712.0000084.00000Nitrogen014.00310.00000Oxygen115.994915.99490Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =0116.12018Exact MassOHfheptan-2-olC7H16OOHOHOH- (C5H11)Rule 8- (CH3)Rule 8- (H )Rule 8OHOHOHHOHH- (H2O)Rule 9

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 5 preview image

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Answers for Student Exercises 1.1 to 1.54Atom Type# of AtomsMassTotal MassHydrogen221.0078322.17226Carbon1112.00000132.00000Nitrogen014.00310.00000Oxygen215.994931.98980Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =1186.16206Exact MassCOOHg3,5,7-trimethyloctanoic acidC11H22O2OHO- (OH )Rule 8- (C10H21)Rule 8- (C9H18)Rule 9COCOOHOCOHOCOHOHOOHHOOHOOHHAtom Type# of AtomsMassTotal MassHydrogen141.0078314.10962Carbon612.0000072.00000Nitrogen014.00310.00000Oxygen115.994915.99490Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =0102.10452Exact MassOHhhexan-1-olC6H14OOHOH- (CH2=CH2) - (H2O)Rule 9- (C5H11)Rule 8- (H )Rule 8H2COHOHHOH

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 6 preview image

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Answers for Student Exercises 1.1 to 1.55Atom Type# of AtomsMassTotal MassHydrogen181.0078318.14094Carbon812.0000096.00000Nitrogen014.00310.00000Oxygen115.994915.99490Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =0130.13584Exact MassOHi2-methylheptan-2-olC8H18OOH- (C5H11)Rule 8- (CH3)Rule 8Rule 8OHOHOHHOH- (H2O)Rule 8- (CH2=C(CH3)2)Atom Type# of AtomsMassTotal MassHydrogen161.0078316.12528Carbon712.0000084.00000Nitrogen014.00310.00000Oxygen015.99490.00000Sulfur131.972131.97210CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =0132.09738Exact MassSjbutyl(propyl)sulfaneC7H16SS- (C3H7)Rule 8- (C2H5)Rule 9- (CH2=CH2)Rule 8SSSHSSH

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 7 preview image

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Answers for Student Exercises 1.1 to 1.56Atom Type# of AtomsMassTotal MassHydrogen201.0078320.15660Carbon1312.00000156.00000Nitrogen014.00310.00000Oxygen115.994915.99490Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =4192.15150Exact MassOHk(2-hexylphenyl)methanolC13H20OAtom Type# of AtomsMassTotal MassHydrogen91.007839.07047Carbon1312.00000156.00000Nitrogen114.003114.00310Oxygen315.994947.98470Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =10227.05827Exact MassONO2l(4-nitrophenyl)(phenyl)methanoneC13H9NO3ONO2- (C6H4NO2)Rule 7&8- (C6H5)Rule 8&9- (CO)Rule 7&8OONO2OONO2OHOHOHHCH2OHCH2- (C5H11)Rule 7- (H2O)Rule 7- (OH )Rule 9OHOHor

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 8 preview image

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Answers for Student Exercises 1.1 to 1.57Atom Type# of AtomsMassTotal MassHydrogen221.0078322.17226Carbon1012.00000120.00000Nitrogen014.00310.00000Oxygen115.994915.99490Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =0158.16716Exact MassOm3-(ethoxymethyl)heptaneC10H22OO- (CH3)Rule 8- (C4H9)Rule 8- (C7H15)Rule 3OOOCH2OOAtom Type# of AtomsMassTotal MassHydrogen191.0078319.14877Carbon1012.00000120.00000Nitrogen014.00310.00000Oxygen115.994915.99490Sulfur031.97210.00000CnHmXxNyOzIHDBromine178.918378.91830Index = (n) - (m/2) - (x/2) + (y/2) + 1 =1234.06197Exact MassHOBrn2-bromodecanalC10H19BrOHOBr- (H )Rule 8- (C8H16)Rule 9- (CO )Rule 9OBrHOBrOBrBrHHOBrHH

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 9 preview image

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Answers for Student Exercises 1.1 to 1.58O- (C6H11O )Rule 8- (CH2=C=O)Rule 8- (CH3)Rule 9OOOOOOO HOOHAtom Type# of AtomsMassTotal MassHydrogen141.0078314.10962Carbon812.0000096.00000Nitrogen014.00310.00000Oxygen215.994931.98980Sulfur031.97210.00000CnHmXxNyOzIHDBromine078.91830.00000Index = (n) - (m/2) - (x/2) + (y/2) + 1 =2142.09942Exact MassoC8H14O2OOcyclohexyl acetate

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 10 preview image

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Answers for Student Exercises 1.6 to 1.119Base PeakMolecularIonFragement IonFragment LossRearrangment7111499 / C6H11O15 / CH386 / C5H1028 / C2H4R71 / C4H7O43 / C3H758 / C3H5O56 / C4H8R43 / C3H771 / C4H7OBase PeakMolecularIonFragement IonFragment LossRearrangment59116 by CI115 / C7H15O1 / H98 / C7H1418 / H2OR87 / C5H11O29 / C2H569 / C5H918 / H2O, 29 / C2H5R59 / C3H7O57 / C4H945 / C2H5O71 / C5H1143 / C3H773 / C4H9O41 / C4H518 / H2O, 57 / C4H9RBase PeakMolecularIonFragement IonFragment LossRearrangment9117091 / C7H779 / BrTropyliumIon75 / C6H380 / HBr, 16 / CH4R65 / C5H579 / Br, 26 / C2H2R50 / C4H2120 / C7H5Br39 / C3H2131 / C4H5BrBase PeakMolecularIonFragement IonFragment LossRearrangment71150121 / C3H6Br29 / C2H5107 / C2H4Br43 / C3H771 / C5H1179 / Br55 / C4H780 / HBr, 16 / CH4R43 / C3H7C2H4Br4-HeptanoneOC7H14OExact Mass: 114.1045IHD = 1, match with (k)AOH3-HeptanolC7H16OExact Mass: 116.1201IHD = 0, match with (m)BBr4-BromotolueneC7H7BrExact Mass: 169.9731IHD = 4, match with (v)CBr2-BromopentaneC5H11BrExact Mass: 150.0044IHD = 0, match with (r)D

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 11 preview image

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Answers for Student Exercises 1.6 to 1.1110Base PeakMolecularIonFragement IonFragment LossRearrangment4310085 / C5H9O15 / CH371 / C4H7O29 / C2H558 / C4H1042 / C2H2OR57 / C3H5O43 / C3H743 / C3H757 / C3H5OBase PeakMolecularIonFragement IonFragment LossRearrangment747473 / C3H5O21 / H57 / C3H5O17 / OH56 / C3H4O18 / H2OR45 / CHO229 / C2H5Base PeakMolecularIonFragement IonFragment LossRearrangment737356 / C4H817 / NH3R55 / C4H718 / NH4R44 / C2H6N29 / C2H543 / C3H730 / CH4NBase PeakMolecularIonFragement IonFragment LossRearrangment5556 by CI55 / C3H3O1 / H39 / C3H317 / OH38 / C3H218 / H2OO2-HexanoneC6H12OExact Mass: 100.0888IHD = 1, match with (h)EOOHPropionic AcidC3H6O2Exact Mass: 74.0368IHD = 1, match with(c)FGH2NC4H11NExact Mass: 73.0896IHD = 0, match with (b)butan-1-amineOHprop-2-yn-1-olC3H4OExact Mass: 56.0264IHD = 2, match with (a)H

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 12 preview image

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Answers for Student Exercises 1.6 to 1.1111Base PeakMolecularIonFragement IonFragment LossRearrangment4389 by CI90 / C3H8NO2Addition of H72 / C3H6NO17 / OHR43 / C3H746 / NO242 / C3H647 / HNO2RBase PeakMolecularIonFragement IonFragment LossRearrangment94138107 / C7H7O31 / CH3O94 / C6H5O44 / C2H4OR77 / C6H561 / C2H5O266 / C5H672 C3H5O2R51 / C4H387 / C4H7O239 / C3H299 / C5H8O2Base PeakMolecularIonFragement IonFragment LossRearrangment9412294 / C6H5O28 / C2H4R77 / C6H545 / C2H5O66 / C5H656 / C3H4O51 / C4H371 / C4H7O39 / C3H283 / C5H8OBase PeakMolecularIonFragement IonFragment LossRearrangment4310287 / C4H7O215 / CH374 / C3H5O228 / C2H4R71 / C4H7O31 / CH3O59 / C2H3O243 / C3H743 / C3H759 / C2H3O2N+OO-1-NitropropaneC3H7NO2Exact Mass: 89.0477IHD = 1, match with (d)IOOH2-PhenoxylethanolJC8H10O2Exact Mass: 138.0681IHD = 4, match with (q)PhenetoleKC8H10OExact Mass: 122.0732IHD = 4, match with (o)OOOMethyl ButyrateLC5H10O2Exact Mass: 102.0681IHD = 1, match with (i)

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 13 preview image

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Answers for Student Exercises 1.6 to 1.1112Base PeakMolecularIonFragement IonFragment LossRearrangment11311385 / C5H11N28 / COR84 / C5H10N29 / CHO56 / C4H857 / C2H3NO55 / C4H758 / C2H4NO42 / C3H671 / C3H5NORBase PeakMolecularIonFragement IonFragment LossRearrangment949467 / C4H5N27 / CHN53 / C3H3N41 / C2H3N42 / C2H4N52 / C3H2N41 / C2H3N53 / C3H3N40 / C2H2N54 / C3H4NBase PeakMolecularIonFragement IonFragment LossRearrangment152152135 / C8H7O217 / OH122 / C7H6O230 / CH2OR107 / C7H7O45 / CHO2R105 / C7H5O17 / OH, 30 / CH2OR92 / C6H4O60 / C2H4O2R77 / C6H517 / OH, 58 /C2H2O263 / C5H389 / C3H5O339 / C3H2113 / C5H6O3Base PeakMolecularIonFragement IonFragment LossRearrangment75 or 157157141 /C6H4ClNO16 / O127 / C6H4O30 / NOR111 / C6H4Cl46 / NO299 / C5H4Cl58 / CNO275 / C6H346 / NO2, 36 / HClR50 / C4H2107 / C2H2ClNO2OHNCaprolactamMC6H11NOExact Mass: 113.0841IHD = 2, match with (j)NN2-methylpyrazineNC5H6N2Exact Mass: 94.0531IHD =4, match with (e)HOOOMethyl salicylateOC8H8O3Exact Mass: 152.0473IHD = 5, match with (s)N+O-OCl1-Chloro-4-NitrobenzenePC6H4ClNO2Exact Mass: 156.9931IHD = 5, match with (t)

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 14 preview image

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Answers for Student Exercises 1.6 to 1.1113Base PeakMolecularIonFragement IonFragment LossRearrangment60208 by CI191 / C7H12OBr17 / OH149 / C5H10Br59 / C2H3O2129 / C7H13O279 /Br111 / C7H11O79 /Br, 18 / H2OR83 / C6H11125 / CH2BrO2R60 / C2H4O2147 / C5H9BrRBase PeakMolecularIonFragement IonFragment LossRearrangment709897 / C6H9O1 / H83 / C5H7O15 / CH379 / C6H719 / H3O70 / C4H6O28 / C2H4Base PeakMolecularIonFragement IonFragment LossRearrangment43126111 / C7H11O15 / CH3108 / C8H1218 / H2OR93 / C7H933 / CH5OR83 / C6H1143 / C2H3O69 / C5H957 / C3H5O58 / C3H6O68 / C5H8R55 / C4H771 C4H7O43 / C2H3O83 / C6H11Base PeakMolecularIonFragement IonFragment LossRearrangment60116 by CI87 / C4H7O229 / C2H573 / C3H5O243 / C3H760 / C2H4O256 / C4H8R45 / CHO271 / C5H11OHOBr7-Bromo Heptanoic AcidQC7H13BrO2Exact Mass: 208.0099IHD = 1, match with (w)HO5-Hexyn-1-olRC6H10OExact Mass: 98.0732IHD = 2, mathc with (g)O6-Methyl-5-hepten-2-oneSC8H14OExact Mass: 126.1045IHD = 2, match with (p)OHOHexanoic acidTC6H12O2Exact Mass: 116.0837IHD = 1, match with (l)

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 15 preview image

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Answers for Student Exercises 1.6 to 1.1114Base PeakMolecularIonFragement IonFragment LossRearrangment162162126 / C6H3OCl36 / HClR98 / C5H3Cl64 / CHOClR63 / C5H399 / CHOCl2Base PeakMolecularIonFragement IonFragment LossRearrangment122122121/C8H9O1 / H107/C7H7O15 / CH391 / C7H731 / CH3O77 / C6H545 / C2H5O65 / C5H557 / C3H5OBase PeakMolecularIonFragement IonFragment LossRearrangment689668 / C4H4O28 / C2H4R55 / C3H3O41 / C3H553 / C4H543 / C2H3O42 / C2H2O54 / C4H6RClClHO2,6-DichlorophenolUC6H4Cl2OExact Mass: 161.9639IHD = 4, match with (u)HO2,6-DimethylphenolVC8H10OExact Mass: 122.0732IHD = 4, match with (n)O2-Cyclohexen-1-oneWC6H8OExact Mass: 96.0575IHD = 3, match with (f)

Solution Manual For Spectrometric Identification of Organic Compounds, 8th Edition - Page 16 preview image

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CHAPTER 22.1𝑣 =12𝜋c√𝑘 (𝑚1𝑚2𝑚1+𝑚2)(k)force constant = 42c2v2meffmeff=(𝑚1𝑚2𝑚1+𝑚2)meff=(1H19F) =(1.0078 x 18.9984)(1.0078 + 18.9984)=0.9570 μmeff=(1H35Cl)=0.9796 μmeff=(1H81Br) =0.9954 μmeff=(1H127I)=0.9999 μ(k)(1H19F) = 4 x 3.142x (2.997 x 1010cm s-1)2x (4148.2 cm-1)2x (0.9570 x 1.66 x 10-27kg)=968.3 kg s-2=968.3 N/m(k)(1H35Cl) = 514.6 N/m(k)(1H81Br) = 410.9 N/m(k)(1H127I) = 313.6 N/mAssume that the force constant for halides are the same when substituting the deuterium -- the calculatedbond stretch frequency for halides:𝑣 =12𝜋c√𝑘 (𝑚1𝑚2𝑚1+𝑚2)2.2.The gross selection rule for infrared activity is that motion corresponding to a normal mode should beaccompanied by a change of dipole moment. So those molecules in which a vibration gives rise to achange in dipole moment are infrared active compounds:(a) CH3CH3, (b) CH4, (c) CH3Cl.It is helpful to write down the structural formulas of the compounds2.3.A nonlinear molecule has 3N-6 normal modes of vibration, where N is the number of atoms in themolecule; a linear molecule has 3N-5.(a) C6H6has 3(12)–6 = 30 normal modes(b) C6H6CH3has 3(16)–6 = 42 normal modes(c) HC≡C-C≡CH is linear; it has 3(6) –5 = 13 normal modes2.4.From top to bottom the:o-xylene,m-xylene, thenp-xylene

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