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TWELVE MORE EASY PROBLEMS

TWELVE MORE EASY PROBLEMS. COMBINED PROBLEMS. FORMULA + INFRARED + NMR. Spectra in these problems were obtained from:. SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (Mar 2002). COMBINED PROBLEM #13. PROBLEM 13 INFRARED SPECTRUM. C 7 H 14 O. 1713. PROBLEM 13 NMR SPECTRUM. 400 MHz.

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TWELVE MORE EASY PROBLEMS

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  1. TWELVE MORE 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)

  3. COMBINED PROBLEM #13

  4. PROBLEM 13 INFRARED SPECTRUM C7H14O 1713

  5. PROBLEM 13 NMR SPECTRUM 400 MHz C7H14O 2 3 2 triplet sextet triplet

  6. COMBINED PROBLEM #14

  7. PROBLEM 14 INFRARED SPECTRUM C7H14O 1716

  8. 6 PROBLEM 14 NMR SPECTRUM C7H14O 1 septet doublet

  9. COMBINED PROBLEM #15

  10. PROBLEM 15 INFRARED SPECTRUM C4H10O

  11. PROBLEM 15 NMR SPECTRUM 3 C4H10O 1 3 2 1 quintet triplet sextet doublet

  12. COMBINED PROBLEM #16

  13. PROBLEM 16 INFRARED SPECTRUM C5H12O

  14. PROBLEM 16 NMR SPECTRUM 90 MHz C5H12O two overlapping multiplets + a singlet* 6 * at 300 MHz you see a nonet, a quartet and a singlet 4 2 triplet doublet

  15. COMBINED PROBLEM #17

  16. PROBLEM 17 INFRARED SPECTRUM C8H10O2

  17. PROBLEM 17 NMR SPECTRUM C8H10O2 3 2 4 1

  18. COMBINED PROBLEM #18

  19. PROBLEM 18 INFRARED SPECTRUM C8H10O

  20. PROBLEM 18 NMR SPECTRUM 3 C8H10O 1 4 2 quartet triplet

  21. COMBINED PROBLEM #19

  22. PROBLEM 19 INFRARED SPECTRUM C6H15N

  23. 6 PROBLEM 19 NMR SPECTRUM C6H15N 4 1 4 triplet sextet triplet

  24. COMBINED PROBLEM #20

  25. PROBLEM 20 INFRARED SPECTRUM C7H9N

  26. PROBLEM 20 NMR SPECTRUM 3 C7H9N 4 2

  27. COMBINED PROBLEM #21

  28. PROBLEM 21 INFRARED SPECTRUM C6H12O2 1737

  29. PROBLEM 21 NMR SPECTRUM C6H12O2 3 1

  30. COMBINED PROBLEM #22

  31. PROBLEM 22 INFRARED SPECTRUM C8H8O2

  32. PROBLEM 22 NMR SPECTRUM 3 C8H8O2 4 1

  33. COMBINED PROBLEM #23

  34. PROBLEM 23 INFRARED SPECTRUM C9H8O 1678 1627

  35. PROBLEM 23 NMR SPECTRUM NOT AVAILABLE AT THIS TIME See if you can’t solve it anyway !

  36. COMBINED PROBLEM #24

  37. PROBLEM 24 INFRARED SPECTRUM C5H6O3 1808 1755 1697

  38. PROBLEM 24 NMR SPECTRUM C5H6O3 4 2 triplet quintet

  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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