1. Drill: Draw & Name Reactants & Products of:
Oxidations of
1-butanol in 2 steps:

2. Drill: Draw & Name Reactants & Products of:
Oxidation of
2-butanol:

3. Drill: Draw & Name 3 isomers containing carboxyl groups of:
C5H10O2

4. Drill: Draw & Name 4 isomers containing carboxyl groups of:
C6H12O2

5. Acid Derivatives

6. Acid Anhydrides

7. Acid Anhydrides
O O
R1-C-O-C-R2

8. Acid Anhydrides
Formed through the dehydration of two carboxylic acids

9. Making Anhydrides
O O
R1-C-OH + HO-C-R2

10. General Anhydride
O O
R1-C-O-C-R2
+ H2O

11. Making Anhydrides O
CH3-C-OH +
HO-C-CH3

12. Diacetic Anhydride
O O
CH3-C-O-C-CH3
+ H2O

13. Succinic
Acid O C
H2C OH
Heat

14. Succinic
Anhydride O C
H2C
O H2O

15. Phthalic
Acid O C OH
Heat

16. Phthalic
Anhydride O C
C H2O O

17. The reverse of the anhydride formation reaction
Anhydride Hydrolysis
The reverse of the anhydride formation reaction

18. Acyl Group O
R-C-

19. Acyl Group O
CH3-C-
Acetyl Group

20. Drill:
Draw the reactants, then predict, draw, & name the product of the dehydration of the combination butanoic acid & propanoic acid.

21. Esters

22. Esters O
R1-C-O-R2

23. The formation of esters
Esterification
The formation of esters

24. Esterification O
R1-C-OH + HO-R2
Acid

25. Ester O
R1-C-O-R2
+ H2O

26. Name R & P O
CH3-C-OH +
HO-CH3
Acid

27. O
Methanol
OH + HO-CH3 OH
HCl
Salicylic Acid

28. Methyl Salicate O
O-CH3
OH + H2O
Oil of Wintergreen

29. Esterification
Acetic
Anhydride O
OH O
C-CH3
OH + O O
Salicylic Acid

30. Acetyl salicylic A O
Acetic acid
OH O +
C-CH3 O HO
C-CH3 O
Aspirin

31. Drill: Draw & name 5 esters that are isomers of C6H12O2

32. Common Esters

33. Ethyl Formate O
H-C-O-CH2-CH3
Rum

34. Octyl acetate O
H3C-C-O-(CH2)7-CH3
Oranges

35. Pentyl acetate O
H3C-C-O-(CH2)4-CH3
Bananas

36. Ethyl butyrate O
H2C-C-O-CH2-CH3
CH2-CH3
Pineapples

37. Pentyl butyrate O
H2C-C-O-(CH2)4-CH3
CH2-CH3
Apricots

38. Methyl butyrate O
H2C-C-O-CH3
CH2-CH3
Apples

39. Predict Product O
CH3-CH2-CH2-C-OH
+ HO-C-CH3 + Heat

40. Common Biological Ester
H2C-OH + HO-C-R1
HC-OH + HO-C-R2
H2C-OH + HO-C-R3

41. Triglyceride O
H2C-O-C-R1
HC-O-C-R2
O H2O
H2C-O-C-R3

42. Common Biological Ester
H2C-OH + HO-PO3-2 O
HC-OH + HO-C-R2
H2C-OH + HO-C-R3

43. Phosphoglyceride
H2C-O-PO3-2 O
HC-O-C-R2
O H2O
H2C-O-C-R3

44. Drill:
Draw the reactants, then predict & draw the products of dehydration synthesis when phenol is added to formic acid.

45. Ester Hydrolysis
Adding water to an ester in acid or base to break it down into an acid & an alcohol

46. Ester Hydrolysis O
R1-C-O-R2
base + H2O

47. Acid & Alcohol O
R1-C-OH + HO-R2

48. A polymer made up of monomers connected by ester bonds
Polyester
A polymer made up of monomers connected by ester bonds

49. Making Polyesters
O O
HO-C-R-C-OH +
HO-R2-OH

50. Thioesters O
R1-C- S-R2

51. Thioesters
In thioesters, the single bonded oxygen is replaced with sulfur

52. Making Thioesters
Addition of a thiol to an acid or an anhydride

53. Acid & Thiol O
R1-C-OH + HS-R2

54. Acid & Thiol O
R1-C-OH + HS-R2

55. Thioesters O
R1-C- S-R2 + H2O

56. Making a Common Thioester
CH3-C-OH + HS-CoA

57. Making a Common Thioester
CH3-C-OH + HS-CoA

58. Acyl Group O
CH3-C-S-CoA
Acetyl CoA

59. Phosphoric Acid O
HO-P-OH OH

60. At pH 7 ish
O O
-O-P-OH & -O-P-O-
OH OH

61. P A Anhydrides
O O
HO-P-OH HO-P-OH
OH OH
Heat

62. P A Anhydrides
O O + H2O
HO-P-O-P-OH
OH OH

63. Phospho Esters O
HO-P-OH + HO-R OH
Heat

64. Phosphoesters O
HO-P-O-R
OH + H2O

65. Phosphodiesters O
HO-P-OH + HO-R
OH + H-O-R

66. Phosphodiesters O
HO-P-O-R
O-R + 2 H2O

67. Transfer of this phosphoryl group through phosphoester bonds
Phosphorylation
Transfer of this phosphoryl group through phosphoester bonds

68. Inorganic Ester
H2C-OH HO-NO2
HC-OH + HO-NO2

69. Nitroglycerin
H2C-O-NO2
HC-O-NO2 + 3 H2O

70. Draw & Name 5 acid or acid derivative containing isomers of:
C3H6O3

71. Drill:
Draw the reactant, then predict, draw, & name the products for the hydrolysis of Propylthioacetate.

72. Acid Review

73. Be familiar with the common acids for matching

74. Be familiar with how to oxidize alcohols

75. Be familiar with DH rxns making acid derivatives

76. Be familiar with hydrolysis of acid derivatives

77. Be able to draw & name isomers with carboxyls

78. Name OH

79. Name OH