MT1Key_Wi01 - NU Winter 2001 To HT 1 2 1(20 pts For each of...

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Unformatted text preview: NU, Winter 2001 To HT 1 2 1. (20 pts) For each of the following sets of mass spectra, match the compounds with their right spectra. Explain your choice using diagram or chemical drawings to illustrate the critical . 7 CW3 fragmentation patterns which allow you to decide. C W M Mlle! CZ (“mm W» . spectrum I WWW (9/ (L 0 i0 20 '30 40 50 60 70 8O 90 l00 110120 130 l40m/e [$0pr WEAK - (Int ML I00 g ' Ax 0 IO 20 30 4O 50 60 70 80 90 100 no 120 l30 l40pI/e ‘ l and 57 :: 191 K+ "(<13 <__. w \h 4..) b 8 g at + P + <9 G) /\ /\ Q 3t 4 F; + \ ® \® Intensnty 01020304050607080901!” m/z NU, Winter 200] 3 2. (30 pts) The following mass spectra are those of three linear (that is, they do not contain branched alkyl substituents) constitutional isomers. They contain only C, H, and 0, gave 69.72 % C and 1 1.70 %H upon elemental analysis. Calculate the common molecular formula for these isomers. Identify the molecular structures of these compounds and match them with their spectra. Explain your choice using diagrams or chemical drawings to illustrate the critical logic/fragmentation patterns which allow you to O decide. It is known that the IR spectra of three compounds all show a very strong absorption at 9 g) l N . . . . approximatel 1710 cm" . However, the IR spectrum that IS assocrated w1th the mass spectrum b) also @ exhibits two low-frequency C—H stretching frequencies around 2720 and 2820 c n 'l W 1+ 60 Wfiéb )GWZVJC M “30%” W": (39 m0 1300:! :5 c: 100 80 100 120 140 160 0‘3 4.7 ' I NU, Winter 2001 4 3. a) (10 pts) The compound that gives rise to the following mass spectrum contains only one carbon atom and two types of halogen. Assign a structure to it and explain your choice using diagrams or chemical drawings to illustrate the critical logic/fragmentation patterns which allow you to decide. b) (10 pts) The mass spectrum of another haloalkane is given below. Assign a structure to this compound and explain your choice using diagrams or chemical drawings to illustrate the critical logic/fragmentation patterns which allow you to decide. NU, Winter 2001 5 4. (10 pts) Match each of the IR spectra shown below to one of the following compounds. Notice that there is no spectrum for two of the compounds. 0 OH a) me C) VKA OH (0M 6) W S ectrumi p ) wavelength, micrometers 2.6 2.8 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13141516 100 r , . 80 60 percent transmxttance .b O i 5’ 31k 20 0 ,CAF L : C, , 380 3400 3000 2600 2200 2000 1800 1600 1400 1200 1000 800 600 wavenumber, cm "1 Spectrum ii) wavelength, micrometers 2.6 2.8 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13141516 100 y . _ , \/\ q) I E’ 80 E a 60 /"\ X f\\ E CW 69 ~ / U : E 20 . c:(>: ,, a. ‘ g E r 0 ’ _ , > . 1 i L . 3 0 3400 000 2600 2200 2000 1800 1600 1400 1200 1000 800 600 Spectrum iii) k b -1 . / / wavenum er, cm / ~/ .9 c c wavelength, micrometers 2.6 2.8 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13141516 100 80 60 <09 0 ‘ * O 3800 3400 3000 2600 2200 2000 1800 1600 1400 1200 1000 800 600 71 0 percent transmittance .4; o wavenumber, cm NU, Winter 2001 6 5. a) (16 pts) Propose a synthesis for the following compound using only cyclohexene and any l-C organic compounds as the only carbon-containing reagents. You may use any inorganic reagent. :‘ I b) (4 pts) Give the major product for ach following reactions. Briefly explain why you chose your answers. ’l K . H f‘ $011 5° MU)“ am 05) L . 0}“ Wm l ’5”) :7 0W M— Nz’lw" :swsri‘ruwo oceans NBS, hv Ga MEN 7 74% W FMOQMHQ WW W? E : NBS,hv \ @ ——_—> C] Macaw D£§[email protected]€'n‘m‘€9 mom; ...
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MT1Key_Wi01 - NU Winter 2001 To HT 1 2 1(20 pts For each of...

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