1. Aldehydes and Ketones

2. Drill Draw & name 5 isomers of: C 3 H 5 OF

3. Aldehydes Organic compounds with carbonyl groups on the end carbon

4. Aldehydes O R-C H

5. Ketones Organic compounds with carbonyl groups within carbon chains

6. Ketones O R-C-R

7. Common Aldehydes

8. Formaldehyde O H-C H Methanal

9. Acetaldehyde O CH 3 -C H Ethanal

10. Propionaldehyde O CH 3 -CH 2 -C H Propanal

11. Butyraldehyde O CH 3 CH 2 CH 2 C H Butanal

12. Benzaldehyde O C H Almond Extract

13. Cinnamaldehyde O

14. all-trans-retinal C=O H

16. all-trans-retinol

17. 4-hydroxy-3-methoxy benzaldehyde Vanillin C O H HO H 3 C-O

18. Draw: acetaldehyde & benzaldehyde

19. Common Ketones

20. Acetone O CH 3 -C CH 3 Propanone

21. Methyl ethyl ketone O CH 3 CH 2 C CH 3 Butanone

22. Cyclohexanone O

23. Benzophenone C O Diphenylmethanone

24. Muscone O

25. General Properties

26. Polarity Alcohols > aldehydes Aldehydes > ketones

27. Solubility in Water Alcohols > aldehydes Aldehydes > ketones

28. Boiling Points Alcohols > aldehydes Aldehydes > ketones

29. Melting Points Alcohols > aldehydes Aldehydes > ketones

30. Oxidation State Alcohols > hydrocarbons Aldehydes > alcohols Acids > aldehydes

31. Show all the oxidation steps in converting butane to 3-butenoic acid

32. Energy State Alcohols < hydrocarbons Aldehydes < alcohols Acids < aldehydes

33. Chm PE Gradient Methane:CH 4 Methanol:CH 3 OH MethanalCH 2 O Methanoic A: HCOOH

34. Chm PE Gradient Reduced Compounds > Less reduced compounds > Oxidized compounds

35. Determine MP order CH 3 -CH 3 CH 3 -CH 2 OH CH 3 -CHO CH 3 -COOH

36. Drill: Draw & name 5 isomers of: C 3 H 9 NO

37. Making Aldehydes & Ketones

38. Oxidation of primary alcohols Making Aldehydes

39. To oxidize alcohols, Hs must be removed from the OH & the adjacent carbon Making Aldehydes

40. OH R-C-H H ox

41. Making Aldehydes OH R-C-H H ox

42. Making Aldehydes OH O R-C-H R-C H H ox

43. Common Oxidizing Agents Cr 2 O 7 -2 MnO 4 -1

44. Examples: K 2 Cr 2 O 7 KMnO 4

45. Oxidation of secondary alcohols Making Ketones

46. OH R-C-R ox H

47. Making Ketones OH O R-C-R R-C R ox H

48. t-Alcohol Ox OH R-C-R R ox

49. t-Alcohol Ox OH R-C-R NR ox R

50. Name reactants & predict & name products H 3 C-OH K 2 Cr 2 O 7 H 2 SO 4

51. Formaldehyde H C=O H Methanal

52. Name reactants & predict & name products H 2 C-OH H 3 C K 2 Cr 2 O 7 H 2 SO 4

53. Acetaldehyde H C=O H 3 C Ethanal

54. Name reactants & predict & name products OH H 3 C-CH-CH 3 K 2 Cr 2 O 7 H 2 SO 4

55. Acetone H 3 C C=O H 3 C Propanone

56. Name reactants & predict & name products K 2 Cr 2 O 7 H 2 SO 4 OH

57. Cyclohexanone O

58. Name reactants & predict & name products K 2 Cr 2 O 7 H 2 SO 4 CH 2 OH

59. Benzaldehyde CHO

60. Aldehyde Detection Reactions

61. Detecting Aldehydes Tollen’s Test Benedict’s & Fehling’s Test Both distinguish aldehydes from ketones

62. Tollen’s Reagent AgNO 3 Ag + + NO 3 - Ag + + 2 NH 3 [Ag(NH 3 ) 2 ] + 100 %

63. Tollen’s Test O R-C-H + 2[Ag(NH 3 ) 2 ] + + 2OH - O NH 4 + R-CO - + 2Ag (s) +3NH 3 + H 2 O

64. Benedict’s Reagent CuSO 4 Cu +2 + SO 4 -2 NaOH Na + + OH - 100 % Fehling’s Reagent

65. Benedict’s Test O R-C-H + 2 Cu +2 + 5 OH - O R-C-O - + Cu 2 O (s) + 3H 2 O

66.  -Hydroxy Ketones HO O R-C-C H R Yield positive results in both tests

67. Drill: Draw  -hydroxy- propanaldehyde

68. Carbonyl Addition Reactions

69. Carbonyl Addition Rxns with water O C + H-OH C HO OH Hydrate

70. Carbonyl Addition Rxns O C + H-OH C HO OH Chloral Hydrate H Cl 3 C Chloral or trichloroacetaldehyde H CCl 3

71. Carbonyl Addition Rxns O C + H-OH H H Methanal

72. Carbonyl Addition Rxns O C + H-OH C HO OH Methanediol H HH H

73. Carbonyl Addition Rxns with alcohols O C + R-OH C RO OH

74. Example O C + OH H 3 C H

75. C H 3 C H HO O

76. Drill: Draw & name 4 isomers C 5 H 10 O that are either aldehydes or ketones:

77. Hemiketal Formation O C + R 3 -OH C R 3 -OOH R 1 R 2 Hemiketal

78. Name reactants & draw products O C + CH 3 -OH H 3 C CH 3

79. O C + CH 3 -OH C H 3 C-OOH H 3 C CH 3 CH 3 Hemiketal

80. Hemiacetal Formation O C + R 3 -OH C R 3 -OOH R 1 H Hemiacetal

81. Hemiacetal Formation O C + R 3 -OH C R 3 -OOH H 3 C H CH 3 H Hemiacetal

82. Hemiacetal Formation O C + R 3 -OH C R 3 -OOH H 3 C H CH 3 H Hemiacetal

83. Draw the reactants & products when water is added to 2-butanone

84. Draw the reactants & products when methanol is added to acetone

85. Full Acetals & Ketals The second addition of an alcohol to either hemi- acetals or ketals will produce full each

86. Uses of Aldehydes & Ketones

87. 1)1-propanol + KMnO 4 2)2-propanol + K 2 Cr 2 O 4 3)2-methyl-2-propanol + K 2 Cr 2 O 4 4) cyclohexanone + water 5)benzaldehyde + water 6)formaldehyde + 1-butanol 7)acetone + phenol 8) 5-hydroxypentanaldehyde (addition)

88. 1)ethanol + KMnO 4 2)2-pentanol + K 2 Cr 2 O 7 3)t-butanol+ K 2 Cr 2 O 7 4) acetone + water 5)formaldehyde + water 6)propanaldehyde + methanol 7) 2-butanone + phenol 8) 4-hydroxybutanaldehyde (addition)

89. Name the following: OH H O

90. Review

91. Name the following: O H OH

92. Draw the following: 3-ethyl-6-methyl- 2-phenoxy-1- sulfhydryl-octa- 4,5-dione

93. Oxidation of each with KMnO 4 or K 2 Cr 2 O 7 : 1-butanol 2-butanol 2-methyl-2-propanol

94. Carbonyl Addition Rxns: 2-butanone + water Propanaldehyde + water Acetone + methanol Acetaldehyde + ethanol

95. Draw the reactants & products when 5- hydroxypentanal reacts with itself

96. Draw & name 3 isomers of C 4 H 8 O containing carbonyls

97. Draw & name 10 isomers of C 4 H 8 O