1. P 100 % P+1 10 % Compound 1 148/13 = 11.38;.38*13 =5 C 11 H 18

2. Compound 1

3. C 11 H 18 C 10 H 14 O Area : 5:2:2:3

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

5. Compound 2 P 100 % P+1: 7.1% P+2 : 33 % 126-35 = 91 91/13 = 7.0 C 7 H 7 Cl

6. Compound 2

7. Area: 5:2

8. Compound 3 m/e 114 114/13 = 8.769; 0.769*13 = 10 C 8 H 18

9. Compound 3

10. C 8 H 18 C 7 H 14 O C 6 H 10 O 2

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

12. Compound 4 m/e 184 184-79 = 105 105/13 = 8.077; 0.077*13 = 1 C 8 H 9 Br

13. Compound 4

14. Area 5:2:2

15. Compound 5 C 8 H 18 O 3 mw 162 m/e 75 C 2 H 3 O 3 + C 3 H 7 O 2 + m/e 73 C 2 HO 3 + C 3 H 5 O 2 + C 4 H 9 O + m/e 147 = P - 15 m/e 130 = P - 32 CH 4 O m/e 115 = P – 47CH 3 O 2 ; C 2 H 7 O

16. Compound 6

17. Compound 7

18. A comparison of two EIMS spectra obtained from different instruments and different samples m/e 136 136/13 = 10.46 0.46*13 = 6 C 10 H 16

19. Compound 7 C 10 H 16

20. Compound 7 C 10 H 16

21. Empirical Rules for Dienes (π → π*) Homoannular(cisoid) Heteroannular (transoid) Parent λ = 253 nm λ = 214 nm Increments for: double bond extension 3030 alkyl subst or ring 55 exocyclic double bond55 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 C 8 H 12

23. Compound 8

24. d d t

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

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

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

29. 282/13 = 21.692; 0.692*13= 9 C 21 H 30 C 18 H 31 Cl C 15 H 32 Cl 2 C 12 H 33 Cl 3 C 9 H 34 Cl 4 C 6 H 35 Cl 5 C 6 Cl 6 35 Cl = 0.76 37 Cl = 0.24 1 1 1n = 1 1 21n = 2 1 3 3 1n = 3 14641n = 4 1 5 10 10 5 1 n = 5 1615201561n = 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%

30. 146/13 = 11.23; 0.23 *13 =3 C 11 H 14 Compound 9 P-28

31. C 11 H 14 C 10 H 10 O Compound 9

32. 2 1 C 10 H 10 O C9H6O2C9H6O2 Compound 9

33. 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 C9H6O2C9H6O2 Compound 9

34. 136/13 = 10.462; 0.462*13 = 6 C 10 H 16 Compound 10

35. Neat liquid

36. Compound 10 C 10 H 16 C 9 H 12 O CCl 4 solution

37. Compound 10 Area: 1:2:2:3 C 9 H 12 O C8H8O2C8H8O2

38. 190.70 D 164.63 S 131.93 D 129.97 S 114.33 D 55.53 Q C8H8O2C8H8O2

39. Compound 11 112/13 = 8.615; 0.615*13 = 8 C 8 H 16

40. Compound 11 C 8 H 16 Degrees of unsaturation: 1

41. Area: 3:2:3 C 8 H 16

42. 147.28 S 126.63 D 123.24 D 122.62 D 23.25 T 16.03 Q C 8 H 16 C 7 H 12 O C 6 H 8 O 2 Exact mass: 112.0347 Exact mass of C 6 H 8 O 2 : 112.0524