Pret he otis na elon empreds. HoH (cry H 0 Scmed' wan Sot, ‘i HW Hy ue ootoet w wilh Len oh-fno o ow” O ewfnemen aitmcumay eta, HL XS 4” Or ro a “ ey “Oo or " a {. fon,Drawing An NMR Spectrum In Learning about NMR spectra, we have seen that chemical shift values can be assigned to specific types of protons, that the areas under peaks are proportional to the numbers of pro- tons, and that nearby protons cause spin-spin splitting. By analyzing the structure of a mo} cule with these principles in mind, you can predict the characteristics of an NMR spectrum, Learning to draw spectra will help you to recognize the features of actual spectra. The process is not difficult if a systematic approach is used. A stepwise method is illustrated here, by drawing the NMR spectrum of the compound shown here. 1. Deter how many types of protons are present, together with their proportions. In the example, there are four types of protons, labeled a,c, and d. The area ratios should shifts of the protons. (Table 13.3 and Appendix 1 serve as guides.) on atom bonded to oxygen; it should absorb around 83 to 64. Protons are less deshielded by the oxygen, probably around 8 1 to 62. Protons ¢ are on a carbon bonded to a carbonyl group; they should absorb around 82.1 t0 62.5. Protons d, one bon removed from a carbonyl, will be deshielded less than protons cand also less than pro- are next to a more strongly deshielded carbon atom, Protons d should absorb Protons a and b split each other into a doublet and a septet, respectively (a typical isopropyl group pattern). Protons c and d split each other into a quartet and a triplet, respectively typical ethyl group pattern). 4, Summarize each absorption order, from the lowest field to the highest. Proton b Protons ¢ Protons a Protons d area 1 2 6 3 chemical shift 34 21-25 12 1 splitting septet quartet doublet triplet 5. Draw the spectrum, using the information from your summary. ‘Work through the following problem to become comfortable with predicting NMR spectra a) Draw the NMR spectra you would expect for the followi (a) (CHy),CH ~O—CH(CHs)> (b) CI—CH—Cr (©) Ph—CH(CHS)> @ cuscno-( verre CH,—COOCH,CH, ©]? 5 CH,—COOCH;CH;