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P 100 % P+1 10 %

Compound 1. P 100 % P+1 10 %. 148/13 = 11.38; .38*13 =5 C 11 H 18. Compound 1. Compound 1. C 11 H 18 C 10 H 14 O. Area : 5:2:2:3. m/e 120 m/e 105 m/e 77. +. m/e 120. m/e 105. Compound 2. P 100 % P+1: 7.1% P+2 : 33 %. 126-35 = 91 91/13 = 7.0 C 7 H 7 Cl. Compound 2.

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P 100 % P+1 10 %

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  1. Compound 1 P 100 % P+1 10 % 148/13 = 11.38; .38*13 =5 C11H18

  2. Compound 1

  3. Compound 1 C11H18 C10H14O Area : 5:2:2:3

  4. m/e 120 m/e 105 m/e 77 +. m/e 120 m/e 105

  5. Compound 2 P 100 % P+1: 7.1% P+2 : 33 % 126-35 = 91 91/13 = 7.0 C7H7Cl

  6. Compound 2

  7. Area: 5:2

  8. Compound 3 m/e 114 114/13 = 8.769; 0.769*13 = 10 C8H18

  9. Compound 3

  10. Compound 3 C8H18 C7H14O C6H10O2

  11. m/e 99 P-15 m/e 86 P-28 m/e 69 P-45 m/e 41 m/e 86 m/e 41 m/e 69

  12. Compound 4 m/e 184 184-79 = 105 105/13 = 8.077; 0.077*13 = 1 C8H9Br

  13. Compound 4

  14. Compound 4 Area 5:2:2

  15. Compound 5 m/e 75 C2H3O3 + C3H7O2+ m/e 73 C2HO3+ C3H5O2+ C4H9O+ m/e 147 = P - 15 m/e 130 = P - 32 CH4O m/e 115 = P – 47 CH3O2; C2H7O C8H18O3 mw 162

  16. Compound 6

  17. Compound 7

  18. m/e 136 136/13 = 10.46 0.46*13 = 6 C10H16 Compound 7 A comparison of two EIMS spectra obtained from different instruments and different samples

  19. C10H16 Compound 7

  20. C10H16 Compound 7

  21. Empirical Rules for Dienes (π → π*) Homoannular(cisoid) Heteroannular (transoid) Parent λ = 253 nm λ = 214 nm Increments for: double bond extension 30 30 alkyl subst or ring 5 5 exocyclic double bond 5 5 Alkenes ethylene λ = 175 nm λ = 253 +10 + 10 = 273 nm

  22. Compound 8 m/e 108 108/13 = 8.3077 0.3077*13 = 4 C8H12

  23. Compound 8

  24. Compound 8 d t d

  25. Compound 8 area = 2:2:4:4 left to right

  26. P : m/e 108 m/e 80 = P-28

  27. 1H NMR: no signal 13C NMR: 4 vinyl carbons

  28. 282/13 = 21.692; 0.692*13= 9 C21H30 C18H31Cl C15H32Cl2 C12H33Cl3 C9H34Cl4 C6H35Cl5 C6Cl6 35Cl = 0.76 37Cl = 0.24 1 1 1 n = 1 1 2 1 n = 2 1 3 3 1 n = 3 1 4 6 4 1 n = 4 1 5 10 10 5 1 n = 5 1 6 15 20 15 6 1 n = 6 n = 5 (0.76)5 = 0.254; 5(0.76)4(0.24)= 0.40 100% 157% n = 6 (0.76)6 = 0.193; 6(0.76)5(0.24) = 0.365 100% 189%

  29. Compound 9 P-28 146/13 = 11.23; 0.23 *13 =3 C11H14

  30. Compound 9 C11H14 C10H10O

  31. Compound 9 2 1 C10H10O C9H6O2

  32. Compound 9 160.63 S 153.99 S 143.48 D 131.79 D 127.95 D 124.43 D 118.81 S 116.70 D 116.56 D C9H6O2

  33. Compound 10 136/13 = 10.462; 0.462*13 = 6 C10H16

  34. Compound 10 Neat liquid

  35. Compound 10 C10H16 C9H12O CCl4 solution

  36. Compound 10 Area: 1:2:2:3 C9H12O C8H8O2

  37. 190.70 D 164.63 S 131.93 D 129.97 S 114.33 D 55.53 Q C8H8O2

  38. Compound 11 112/13 = 8.615; 0.615*13 = 8 C8H16

  39. Compound 11 C8H16 Degrees of unsaturation: 1

  40. Area: 3:2:3 C8H16

  41. 147.28 S 126.63 D 123.24 D 122.62 D 23.25 T 16.03 Q C8H16 C7H12O C6H8O2 Exact mass: 112.0347 Exact mass of C6H8O2: 112.0524

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