1. Drill
Draw & name 5 isomers of:
C3H5OF

2. Test 6 is attached to the Poly website
Test 6 is attached to the Poly website. Complete it & turn it in tomorrow.

3. Aldehydes and Ketones

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

5. Aldehydes O
R-C H

6. Organic compounds with carbonyl groups within carbon chains
Ketones
Organic compounds with carbonyl groups within carbon chains

7. Ketones O C
R R

8. Common Aldehydes

9. Formaldehyde O
H-C H
Methanal

10. Acetaldehyde O
CH3-C H
Ethanal

11. Propionaldehyde O
CH3-CH2-C H
Propanal

12. Butyraldehyde O
CH3CH2CH2C H
Butanal

13. Benzaldehyde O C H
Almond Extract

14. Cinnamaldehyde O

15. 4-hydroxy-3-methoxy benzaldehyde
H3C-O O C HO H
Vanillin (Vanilla)

16. all-trans-retinal H
C=O

17. all-trans-retinol H
C-OH H

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 >
Ketones

27. Solubility in Water
Alcohols >
Aldehydes >
Ketones

28. Boiling Points
Alcohols >
Aldehydes >
Ketones

29. Melting Points
Alcohols >
Aldehydes >
Ketones

30. Oxidation State
Acids >
Aldehydes >
Alcohols >
hydrocarbons

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

32. Energy State
Acids <
Aldehydes <
Alcohols <
hydrocarbons

33. Chm PE Gradient Methane: CH4 > Methanol: CH3OH >
Methanal CH2O >
Methanoic A: HCOOH

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

35. Organic HW Draw & name 3 different aldehydes & 3
ketones that are isomers
of the aldehydes.

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

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

38. Making Aldehydes & Ketones

39. Making Aldehydes
Oxidation of primary alcohols

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

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

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

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

44. Common Oxidizing Agents
Cr2O7-2
MnO4-1

45. Examples:
K2Cr2O7
KMnO4

46. Oxidation of secondary alcohols
Making Ketones
Oxidation of secondary alcohols

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

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

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

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

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

52. Formaldehyde H
C=O
Methanal

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

54. Acetaldehyde H
C=O
H3C
Ethanal

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

56. Acetone
H3C
C=O
Propanone

57. Name reactants & predict & name productsOH
K2Cr2O7
H2SO4

58. Cyclohexanone O

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

60. Benzaldehyde
CHO

61. Name reactants & predict & name productsOH
K2Cr2O7
H2SO4

62. 1-methyl-1-cyclopentanol
Organic HW: Draw reactants & draw & name products for the oxidation of each of:
1-pentanol
Cyclopentanol
1-methyl-1-cyclopentanol

63. Drill: Draw reactants & draw & name products for the oxidation of each of:
1-butanol
2-butanol
2-methyl-2-butanol

64. Aldehyde Detection Reactions

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

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

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

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

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

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

71. a-hydroxy-propanaldehyde
Drill: Draw
a-hydroxy-propanaldehyde

72. Carbonyl Addition Reactions

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

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

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

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

77. Cyclohexanone Acetaldehyde formaldehyde
Organic HW: Draw the reactants, then predict, draw, & name the products for the addition of water to each of the following:
Cyclohexanone
Acetaldehyde
formaldehyde

78. acetone propanaldehyde cyclopropanone
Drill: Draw the reactants, then predict, draw, & name the products for the addition of water to each of the following:
acetone
propanaldehyde
cyclopropanone

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

80. Example O
C OH
H3C H

81. HO O C
H3C H

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

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

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

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

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

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

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

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

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

91. Schedule
Modeling lab tomorrow
Review Monday
Test Tuesday

92. Butanaldehyde Butanone
Organic HW: Draw the reactants, then draw & name the organic products when: ethanol reacts with:
Butanaldehyde
Butanone

93. Modeling Lab on Aldehydes & Ketones

94. Drill: Draw reactants, then draw & name the products for each of the following:
Addition of phenol to cyclopentanone
Oxidation of ethanol

95. Identify certain aldehydes & ketones:

96. Formaldehyde Acetaldehyde Benzaldehyde Acetone

97. Draw organic reactants, then draw & name major organic products.

98. + K2Cr2O7 3) 2-methyl-2-propanol 1) 1-propanol + KMnO4
2) 2-propanol + K2Cr2O7
3) 2-methyl-2-propanol
+ K2Cr2O7
4) cyclohexanone + water

99. 5) benzaldehyde + water 6) formaldehyde + 1-butanol
7) acetone + phenol
5-hydroxypentanaldehyde
(addition)

100. 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)

101. Draw & Name 10 Carbonyl Containing Isomers of:
C6H12O

102. Drill: Name the following:OH OH

103. Review for Tomorrow’s Test

104. Name the following: OH O H

105. 3-ethyl-6-methyl-2-phenoxy-1-sulfhydryl-octa-4,5-dione
Draw the following:
3-ethyl-6-methyl-2-phenoxy-1-sulfhydryl-octa-4,5-dione

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

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

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

109. Draw & name 5 isomers of C5H10O containing carbonyls

110. Draw & name 10 isomers of C4H8O