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Chemistry 2100 Chapter 17.

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Presentation on theme: "Chemistry 2100 Chapter 17."— Presentation transcript:

1 Chemistry 2100 Chapter 17

2

3 Nomenclature IUPAC names for aldehydes
To name an aldehyde, change the suffix -e of the parent alkane to -al. Because the carbonyl group of an aldehyde can only be at the end of a parent chain and numbering must start with it as carbon-1, there is no need to use a number to locate the aldehyde group. For unsaturated aldehydes, indicate the presence of a carbon-carbon double bond by changing the ending of the parent alkane from -ane to -enal. Numbering the carbon chain begins with the aldehyde carbonyl carbon. Show the location of the carbon-carbon double bond by the number of its first carbon.

4 Nomenclature The IUPAC system retains common names for some aldehydes, including these three.

5 Nomenclature IUPAC names for ketones.
The parent alkane is the longest chain that contains the carbonyl group. Indicate the presence of the carbonyl group by changing the -ane of the parent alkane -one. Number the parent chain from the direction that gives the carbonyl carbon the smaller number. The IUPAC retains the common name acetone for 2-propanone.

6 Nomenclature To name an aldehyde or ketone that also contains an -OH (hydroxyl) or -NH2 (amino) group: Number the parent chain to give the carbonyl carbon the lower number. Indicate an -OH substituent by hydroxy-, and an -NH2 substituent by amino-. Hydroxyl and amino substituents are numbered and alphabetized along with other substituents.

7 Nomenclature Common names
The common name for an aldehyde is derived from the common name of the corresponding carboxylic acid. Drop the word "acid" and change the suffix -ic or -oic to -aldehyde. Name each alkyl or aryl group bonded to the carbonyl carbon as a separate word, followed by the word "ketone”. Alkyl or aryl groups are generally listed in order of increasing molecular weight.

8 Physical Properties

9 Physical Properties

10 p. 461

11 Preparations

12 (1°) (2°)

13 (1°) (2°)

14 (1°) (2°)

15 (1°) (2°)

16 (1°) (2°)

17 Reactions

18 Z = C, H

19   Z = C, H

20   Z = C, H

21     Z = C, H

22     Z = C, H

23     Z = C, H

24     Z = C, H

25     Z = C, H

26     Z = X, O, N

27     OH Z = X, O, N

28

29

30  

31    

32    

33    

34    

35    

36    

37    

38

39

40 (xs)

41 (xs)

42 (xs)

43 Cyclization

44  

45    

46    

47    

48    

49    

50    

51    

52 1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6

53 1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6

54 1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6

55 1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6

56 1 6 6 2 5 5 3 1 4 4 1 4 3 2 3 2 5 6

57 1 6 2 5 3 4 1 4 3 2 5 6

58 1 6 6 6 4 2 5 5 5 3 1 4 4 1 3 4 2 3 2 3 2 1 5 6

59 Reduction The carbonyl group of an aldehyde or ketone is reduced to an -CHOH group by hydrogen in the presence of a transition-metal catalyst. Reduction of an aldehyde gives a primary alcohol. Reduction a ketone gives a secondary alcohol.

60 Reduction Reduction by NaBH4 does not affect a carbon-carbon double bond or an aromatic ring.

61 Tollens Benedict

62 Keto-Enol Tautomerism

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64

65

66

67

68

69

70 "enolizable"

71 "enolizable"

72 "enolizable"

73 "enolizable"

74 "enolizable"

75 "enolizable"

76 "enolizable"

77 tautomers "enolizable"

78 ?

79 ?

80 H

81 H H H H

82 H H H H H H

83 H H H H H H

84 H H H H H H

85

86 enediol

87 H enediol

88 H enediol

89 H enediol

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91

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