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TWELVE EASY PROBLEMS

TWELVE EASY PROBLEMS. COMBINED PROBLEMS. FORMULA + INFRARED + NMR. Spectra in these problems were obtained from:. SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (Mar 2002). NOTE ON INTEGRALS:. Integrals (relative number of hydrogens) are given as: 2.

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TWELVE EASY PROBLEMS

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  1. TWELVE EASY PROBLEMS COMBINED PROBLEMS FORMULA + INFRARED + NMR

  2. Spectra in these problems were obtained from: SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (Mar 2002) NOTE ON INTEGRALS: Integrals (relative number of hydrogens) aregiven as: 2 The integrals are the simplest ratio. Expansions are blue and printed above the baseline.

  3. COMBINED PROBLEM #1

  4. PROBLEM 1 INFRARED SPECTRUM C4H10O

  5. PROBLEM 1 NMR SPECTRUM 6 C4H10O 2 1 1 doublet multiplet doublet

  6. COMBINED PROBLEM #2

  7. PROBLEM 2 INFRARED SPECTRUM C9H10O2 1719

  8. PROBLEM 2 NMR SPECTRUM C9H10O2 3 2 5 two multiplets quartet triplet

  9. COMBINED PROBLEM #3

  10. PROBLEM 3 INFRARED SPECTRUM C10H12O 1688

  11. 6 PROBLEM 3 NMR SPECTRUM C10H12O 5 1 septet doublet

  12. COMBINED PROBLEM #4

  13. PROBLEM 4 INFRARED SPECTRUM C5H10O2 1712

  14. PROBLEM 4 NMR SPECTRUM 3 C5H10O2 1 2 two overlapping multiplets (2 + 2) 4 triplet triplet

  15. COMBINED PROBLEM #5

  16. PROBLEM 5 INFRARED SPECTRUM C9H12

  17. PROBLEM 5 NMR SPECTRUM C9H12 6 5 1 septet doublet

  18. COMBINED PROBLEM #6

  19. PROBLEM 6 INFRARED SPECTRUM C9H12 1610

  20. PROBLEM 6 NMR SPECTRUM 3 C9H12 1

  21. COMBINED PROBLEM #7

  22. PROBLEM 7 INFRARED SPECTRUM C6H10O3 1731 1719

  23. PROBLEM 7 NMR SPECTRUM 3 C6H10O3 3 2 2 triplet quartet

  24. COMBINED PROBLEM #8

  25. PROBLEM 8 INFRARED SPECTRUM C5H7NO2 2266 1749

  26. PROBLEM 8 NMR SPECTRUM C5H7NO2 2 3 2 quartet triplet

  27. COMBINED PROBLEM #9

  28. PROBLEM 9 INFRARED SPECTRUM C9H12O

  29. PROBLEM 9 NMR SPECTRUM C9H12O 5 3 2 1 1 triplet quintet triplet

  30. COMBINED PROBLEM #10

  31. PROBLEM 10 INFRARED SPECTRUM C8H12O4 1730

  32. PROBLEM 10 NMR SPECTRUM 400 MHz 3 C8H12O4 1 2 quartet triplet

  33. COMBINED PROBLEM #11

  34. PROBLEM 11 INFRARED SPECTRUM C7H12O4 1735

  35. PROBLEM 11 NMR SPECTRUM 400 MHz 3 C7H12O4 1 2 quartet triplet

  36. COMBINED PROBLEM #12

  37. PROBLEM 12 INFRARED SPECTRUM C8H7N 2229

  38. PROBLEM 12 NMR SPECTRUM 400 MHz 3 C8H7N 4

  39. CORRELATION CHARTS

  40. BASIC INFRARED KNOWLEDGE EXPANDED CH 3000 BASE VALUES OH 3600 NH 3400 CH 3000 C N 2250 C C 2150 C=O 1715 C=C 1650 C-O 1100 3300 3100 2900 2850 2750 C-H =C-H -C-H -CHO CH2 and CH3 bend :1465and1365 1800 1735 1725 1715 1710 1690 aldehyde acid acid chloride ester amide ketone anhydride : 1810 and 1760 EXPANDED C=O benzene C=C : between1400and1600 Also remember the effects of H-bonding, conjugation and ring size.

  41. NMR Correlation Chart -OH -NH DOWNFIELD UPFIELD DESHIELDED SHIELDED CHCl3 , TMS d (ppm) 12 11 10 9 8 7 6 5 4 3 2 1 0 H CH2Ar CH2NR2 CH2S C C-H C=C-CH2 CH2-C- CH2F CH2Cl CH2Br CH2I CH2O CH2NO2 C-CH-C RCOOH RCHO C=C C C-CH2-C C-CH3 O Ranges can be defined for different general types of protons. This chart is general, the next slide is more definite.

  42. O O O O O O O APPROXIMATE CHEMICAL SHIFT RANGES (ppm) FOR SELECTED TYPES OF PROTONS R-CH3 0.7 - 1.3 R-N-C-H 2.2 - 2.9 R-C=C-H R-CH2-R 1.2 - 1.4 4.5 - 6.5 R-S-C-H 2.0 - 3.0 R3CH 1.4 - 1.7 I-C-H 2.0 - 4.0 H R-C=C-C-H 1.6 - 2.6 Br-C-H 2.7 - 4.1 6.5 - 8.0 Cl-C-H 3.1 - 4.1 R-C-C-H 2.1 - 2.4 R-C-N-H RO-C-H 3.2 - 3.8 5.0 - 9.0 RO-C-C-H 2.1 - 2.5 HO-C-H 3.2 - 3.8 R-C-H HO-C-C-H 2.1 - 2.5 9.0 - 10.0 R-C-O-C-H 3.5 - 4.8 N C-C-H 2.1 - 3.0 O2N-C-H 4.1 - 4.3 R-C-O-H R-C C-C-H 2.1 - 3.0 11.0 - 12.0 F-C-H 4.2 - 4.8 C-H 2.3 - 2.7 R-N-H 0.5 - 4.0 Ar-N-H 3.0 - 5.0 R-S-H R-O-H 0.5 - 5.0 Ar-O-H 4.0 - 7.0 1.0 - 4.0 R-C C-H 1.7 - 2.7

  43. m 10 11 12 13 14 15 ALKENES s s Monosubstituted Disubstituted cis-1,2- s trans-1,2- s 1,1- s Trisubstituted m =C-H OUT OF PLANE BENDING Tetrasubstituted 1000 900 800 700 cm-1

  44. m 10 11 12 13 14 15 BENZENES Monosubstituted s s Disubstituted s ortho m s s meta para s RING H’s Trisubstituted OOPS m s 1,2,4 1,2,3 s m 1,3,5 s m combination bands 1000 900 800 700 cm-1

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