1. 1 1)

2. 2 2) 3)

3. 3 Ag 2 O and NH 4 OH are the Tollens reagent 4) 5)

4. 4 6) Draw sodium acetate. 7) Draw cycloheptanecarboxylic acid.

5. 5 8) Draw 4-hexenal. 9) Draw 2,4-pentanedione.

6. 6 10) Draw benzene-1,3-dicarboxaldehyde. 11) Draw the product(after workup) of 3-methyl-2-cyclohexenone with methyl Grignard.

7. 7 12) Draw the product(after workup) of 3-methyl- 2-cyclohexenone with H 2./Pd-C. 13) Draw the keto tautomer of this enol.

8. 8 14) Pentane-2,4-dione exists as a tautomeric mixture of 8% keto and 92% enol. Draw the enol form. The Z isomer is preferred due to the stabilization provided by hydrogen bonding.

9. 9 15) 16)

10. 10 17) 18)

11. 11

12. 12 19)

13. 13

14. 14 20)

15. 15 19..29a) Draw 3,3’-dimethylpentanoic acid. e) Draw m-hydroxybenzoic acid

16. 16 19.32a) b) c)

17. 17 d) 19.33a) b)

18. 18 c).

19. 19 19.37) In each group choose which compound is most acidic. Also choose which has the strongest conjugate base. a) Most acidic Strongest conjugate base b) Most acidic Strongest conjugate base

20. 20 20.37) No reaction

21. 21 No reaction

22. 22 20.38) No reaction

23. 23 No reaction

24. 24 20.40)

25. 25 20.41) No reaction

26. 26 20.47)

27. 27 21.46)

28. 28

29. 29 21.54)

30. 30

31. 31 1)

32. 32

33. 33 2)

34. 34 3)

35. 35 4)

36. 36 5)

37. 37 6)

38. 38 7)

39. 39 8)

40. 40 9)

41. 41 10)

42. 42 11)

43. 43 12)

44. 44 13)

45. 45 14)

46. 46 15)

47. 47

48. 48 22.53) a) b)

49. 49 c) d)

50. 50 e) f)

51. 51 g) h)

52. 52 i) j)

53. 53 k) l)

54. 54 22.54)

55. 55

56. 56

57. 57