MASS S PECTROMETRY (MS) - Xander

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MASS SPECTROMETRY (MS)Exercise 1:Determine the degree of unsaturation (IHD) for the hydrocarbons with the following molecularformulas:(a) C10H16HDI 3(b) C7H7NOHDI 5(c) C8H9ClOHDI 4Exercise 2:An unknown substance shows a molecular ion peak at m/z 170 with a relative intensity of 100.The M 1 peak has an intensity of 13.2, and the M 2 peak has an intensity of 1.00. What is themolecular formula of the unknown?M at m/z 170M peakM 1 peakM 2 peakimplies an even # of nitrogenit is the base peak, no recalculation necessary13.2 / 1.1 12; 12 carbons1.00% of M ; no S, Cl, Br170 – (12)(12) 26cannot have two NM 2 peak170 – (12)(12) – 16 10C12H26 is possibleMM exceededits presence might indicate oxygenC12H10Oanswer: C12H10O (or C12H26)Exercise 3:An unknown hydrocarbon has a molecular ion peak at m/z 84, with a relative intensity of 31.3.The M 1 peak has a relative intensity of 2.06, and the M 2 peak has a relative intensity of 0.08. Whatis the molecular formula for this substance?M at m/z 84M peakM 31.3M 12.06M 20.0884 – (6)(12) 12implies an even # of nitrogenit is not the base peak, recalculation necessary100%6.58%6.58 / 1.1 5.98; 6 carbons0.25%no S, Cl, Branswer: C6H12Page 1

Exercise 4:An unknown substance has a molecular ion peak at m/z 107, with a relative intensity of 100. Therelative intensity of the M 1 peak is 8.00, and the relative intensity of the M 2 peak is 0.30. What isthe molecular formula for this unknown?M at m/z 107implies an odd # of nitrogenM peakit is the base peak, no recalculation necessaryM 1 peak8.00 / 1.1 7.3; 7 carbonsM 2 peak0.30%; no S, Cl, Br107 – (1)(14) – (7)(12) 9answer: C7H9NExercise 5:The mass spectral data of an unknown liquid are given below. What is the molecular formula of thisunknown?M at m/z 78M peakM 23.6M 10.79M 27.5578 – (3)(12) – 35 7implies an even # of nitrogenit is not the base peak, recalculation necessary100%3.35%3.35 / 1.1 3.05; 3 carbons32%Cl is presentanswer: C3H7ClExercise 6:Propose a molecular formula for each mass spectrum:Page 2

Exercise 7:Look at the mass spectrum of 2-methylhexane. What is the m/z value of the M peak and of the basepeak? Give possible structures of the fragments giving rise to the large peaks at m/z 85, 57, and 43.M peakm/z 100base peakm/z 43Page 3

Exercise 8:Give the structure of the molecule that gives the following mass spectrum.Exercise 9:The mass spectra of heptane and 2,2,3-trimethylbutane are given below. Which spectrum representswhich compound? Explain.Page 4

Exercise 10:Propose a structure for the compound having the following mass spectrum:(a)(b)Page 5

MASS S PECTROMETRY (MS) Exercise 1: Determine the degree of unsaturation (IHD) for the hydrocarbons with the following molecular formulas: (a) C10 H16 HDI 3 (b)C7H7NO HDI 5 (c) C8H9ClO HDI 4 Exercise 2: An unknown substance shows a molecular ion peak at m/z 170 with a relative intensity of 100. The M 1 peak has an intensity of 13.2, and the M 2 peak has an intensity of 1.00.

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