Question

wolned Spectra Problems it all together": mbined Spectra Problems The Combin friends, the moment has come... During the past two semesters, we have talked about infrared spectros- y (IR), 'H-NMR spectroscopy, "C-NMR spectroscopy, and Mass spec- trometry (MS). We've also talked about using information gathered from the mass spectrum to generate a molecular formula and the index of hydro- gen deficiency which helps us determine information about our compound when there isn't any available. The moment has come in which we piece all of these together. There are 8 problems in this chapter, each problem comes with an IR, both H- and C-NMR spectra, and a mass spectrum. With this information, you need to do the following for each problem: • Identify all major functional groups in the IR spectra • Identify all peaks in 'H- and "C-NMR spectra • Identify the molecular mass of the unknown from the mass spectrum • Determine the pattern of fragmentation from the mass spectrum • Generate a molecular formula • Determine the Index of Hydrogen Deficiency • Determine the structure of the unknown compound. You will need to do your work on a separate sheet of paper. While you can write on the spectra, your TAs will grade your written work. Good luck!!

Answer 1

. I ☺ the structure of compound is 164-chlorophenylethanore 4 chlorpopaletophenone. IR! The peak at near by room is for co group. The peak at near by 1600 cm' is for C=c group. Hi g h The 3 Ha hydrogen Comes at near by = " 2.5ppm as Singlet.. - the 2 Ho hydrogen Cases as a by 8ppm The & Hc hy arosen Comes as doublet at near by 7.4ppen . a carbon Emes at nearby 25ppm 4 carton Cerrus at nearby 205ppm 1 C₂ Casson comes at near by 135ppm deutlet at near ne a Ho hydrogen comes as > 132 12 cu carton Cannat near by 135 ppm 7265 Carbon Conces at nearty 125ppm - Co Cashen Corms at nearby 140 ppm. mass! molicate ma peak and m+2 peak 1: 3 presence of chlesine Cg Hclo Boxe en 12x8 + 1x7 + 8 x 35 +14 16 = 154 (m) + C H CH 0 Tu EU = 139, 1403-=11 )*- 750 Index of hydrogen desiconly. = 2n+2 - Hox = 2(8)+2-7-1 -- 18-8= 5 18-8 .5 3 deuble benas t x = halosey. 2 one CEO

® the structure of contacon compound pentan-2-one IR peak at near by 2900ant is for C-H group - peak at mear by 1700 cm' is for c=0 group á % d - The 3 Ha hidrosen Grnes as singlet at near - by appm the Q Ho hydrogen comes as triplet at near by 204899 - The Q He hojarozen Games as multiplet at nearby 1.5ppm - the 3 Hd hyaroren Cemer as tright at near by Iren. a3 :. í 4 a carbon amis at 308fm í ž 5 C₂ Carbon Cames at 205ppm C Carbon termes at 45ppm ao carson Cosas at 15 ppm - Cu Carban Cermon at 2011m mass: meat is given at 86 p . m = 86 ir cs HiGo indstillo this = 86 - 43 art. 71; (w)* = 58 : [= 43 ma 71 * Inles of hydrogen deficiency. = 2n +2 -1 = no.de Canbay. -= 265) +2-10 = 12-10= 1 2 the structure of unknown Comeporena 15 petan-2-one - [5 Hoo12x5t IXLot 7 + 2.