1. Aldehydes and Ketones

2. Drill
Draw & name 5 isomers of:
C3H5OF

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

4. Aldehydes O
R-C H

5. Organic compounds with carbonyl groups within carbon chains
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
CH3-C H
Ethanal

10. Propionaldehyde O
CH3-CH2-C H
Propanal

11. Butyraldehyde O
CH3CH2CH2C H
Butanal

12. Benzaldehyde O C H
Almond Extract

13. Cinnamaldehyde O

14. all-trans-retinal H
C=O

16. all-trans-retinol

17. 4-hydroxy-3-methoxy benzaldehyde
H3C-O O C HO H
Vanillin

18. Draw: acetaldehyde & benzaldehyde

19. Common Ketones

20. Acetone O
CH3-C
CH3
Propanone

21. Methyl ethyl ketone O
CH3CH2C
CH3
Butanone

22. Cyclohexanone O

23. Benzophenone O C
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: CH4 Methanol: CH3OH Methanal CH2O
Methanoic A: HCOOH

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

35. Determine MP order
CH3-CH3
CH3-CH2OH
CH3-CHO
CH3-COOH

36. Drill:
Draw & name 5 isomers of:
C3H9NO

37. Making Aldehydes & Ketones

38. Making Aldehydes
Oxidation of primary alcohols

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

40. Making Aldehydes 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
Cr2O7-2
MnO4-1

44. Examples:
K2Cr2O7
KMnO4

45. Oxidation of secondary alcohols
Making Ketones
Oxidation of secondary alcohols

46. Making Ketones 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
K2Cr2O7
H2SO4
H3C-OH

51. Formaldehyde H
C=O
Methanal

52. Name reactants & predict & name products
K2Cr2O7
H2SO4
H2C-OH
H3C

53. Acetaldehyde H
C=O
H3C
Ethanal

54. Name reactants & predict & name productsOH
H3C-CH-CH3
K2Cr2O7
H2SO4

55. Acetone
H3C
C=O
Propanone

56. Name reactants & predict & name productsOH
K2Cr2O7
H2SO4

57. Cyclohexanone O

58. Name reactants & predict & name products
CH2OH
K2Cr2O7
H2SO4

59. Aldehyde Detection

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

61. Tollen’s Reagent
AgNO Ag+ + NO3-
Ag+ + 2 NH3
[Ag(NH3)2]+
100 %

62. Tollen’s Test R-C-H + 2[Ag(NH3)2]+ + 2OH- O
NH4+R-CO- + 2Ag(s)+3NH3 + H2O

63. Benedict’s Reagent CuSO4 Cu+2 + SO4-2 NaOH Na+ + OH- Fehling’s Reagent
100 %
100 %
Fehling’s Reagent

64. Benedict’s Test O
R-C-H + 2 Cu OH-
R-C-O- + Cu2O(s) + 3H2O

65. Yield positive results in both tests
a-Hydroxy Ketones
HO O
R-C-C
H R
Yield positive results in both tests

66. Carbonyl Addition Reactions

67. Carbonyl Addition Rxns with water
C H-OH C
Hydrate HO OH

68. Carbonyl Addition Rxns
Chloral or
trichloroacetaldehyde O
C + H-OH H
Cl3C H
CCl3 C
Chloral
Hydrate HO OH

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

70. Carbonyl Addition Rxns
C + H-OH H H H H C
Methanediol HO OH

71. Carbonyl Addition Rxns with alcohols
C R-OH C RO OH

72. Example O
C OH
H3C H

73. HO O C
H3C H

74. Draw & name 4 isomers C5H10O that are either aldehydes or ketones:
Drill:
Draw & name 4 isomers C5H10O that are either aldehydes or ketones:

75. Hemiketal Formation O
C R3-OH
R R2
R R2 C
Hemiketal
R3-O OH

76. Name reactants & draw products
C CH3-OH
H3C CH3

77. O
C CH3-OH
H3C CH3
CH CH3 C
Hemiketal
H3C-O OH

78. Hemiacetal Formation O
C R3-OH
R H
R H C
Hemiacetal
R3-O OH

79. Hemiacetal Formation O
C R3-OH
H3C H
CH H C
Hemiacetal
R3-O OH

80. Hemiacetal Formation O
C R3-OH
H3C H
CH H C
Hemiacetal
R3-O OH

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

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

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

84. Uses of Aldehydes & Ketones

85. 6) formaldehyde + 1-butanol
1) 1-propanol + KMnO4
2) 2-propanol + K2Cr2O4
3) 2-methyl-2-propanol + K2Cr2O4
4) cyclohexanone + water
5) benzaldehyde + water
6) formaldehyde + 1-butanol
7) acetone + phenol
8) 5-hydroxypentanaldehyde (addition)

86. 6) propanaldehyde + methanol
1) ethanol + KMnO4
2) 2-pentanol + K2Cr2O7
3) t-butanol+ K2Cr2O7
4) acetone + water
5) formaldehyde + water
6) propanaldehyde + methanol
7) 2-butanone + phenol
8) 4-hydroxybutanaldehyde (addition)

87. Name the following: O OH H

88. Review

89. Name the following: OH O H

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

91. Oxidation of each with KMnO4 or K2Cr2O7:
1-butanol
2-butanol
2-methyl-2-propanol

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

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

94. Draw & name 5 isomers of C4H8O containing carbonyls