MT1_Wi01 - NU, Winter 2001 2 1. (20 pts) For each of the...

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Unformatted text preview: NU, Winter 2001 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 fragmentation patterns which allow you to decide. spectrum I 0 lo 20 '30 40 50 60 70 80 90 IOO MO 120 130 l40m/e 80 spectrum 2 0 IO 20 30 40 SO 60 70 80 90 100 HO IZO 130 MOM/c Intensity 0 10 20 30 40 50 60 70 80 90 100 m/z Intensity 0.102030405060708090100 m/I 100 8888 O IN 8888 O 100 8888 O NU, Winter 2001 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 11.70 %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 decide. It is known that the IR spectra of three compounds all show a very strong absorption at approximately 1710 cm‘l. However, the IR spectrum that is associated with the mass spectrum b) also exhibits two low-frequency C-H stretching frequencies around 2720 and 2820 cm'l. a) 20 40 so so 100 120 140 160 b) 20 4o 60 so 100 120 140 160 C) 20 4o 60 so 100 120 140 160 NU, Winter 200] 3. a) (l 0 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. 100 80 60 4O 20 O 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. 100 so 60 40 20 0 NU, Winter 200] 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) mo C) W OH (Um e) W Spectrum i) wavelength, micrometers 2.6 2.8 3 3.5 4 4.5 5 5.5 6 7 8 9 10 ll 12 13141516 100 ~ , , 0.) E 80 8 60 c E 2 40 x: 8 E 20 D. 0 , 3800 3400 3000 2600 2200 2000 1800 1600 1400 1200 1000 800 600 wavenumber, cm’l 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 r ‘ Q) E 80 S 60 r: E :1 40 c: 8 B 20 an ... 3800 3400 3000 2600 2200 2000 1800 1600 1400 1200 1000 800 Spectrum 111) wavenumber, cm‘1 wavelength, micrometers 2.6 2.8 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13141516 100 - ' 0) E 80 S 60 a S :3 40 x: 3 B 20 D4 . 0 3800 3400 3000 2600 2200 2000 1800 1600 1400 1200 1000 800 600 A1 wavenumber, cm NU, Winter 2001 NA-MQ 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. O\/\/\/\O b) (4 pts) Give the major product for each of following reactions. Briefly explain why you chose your answers. NBS, hv :>: NBS, hv ...
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MT1_Wi01 - NU, Winter 2001 2 1. (20 pts) For each of the...

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