7/25/2019 Aldehyde Keton

1/75

Based on McMurrys Organic Chemistry, 7th

edition

7/25/2019 Aldehyde Keton

2/75

7/25/2019 Aldehyde Keton

3/75

7/25/2019 Aldehyde Keton

4/75

7/25/2019 Aldehyde Keton

5/75

7/25/2019 Aldehyde Keton

6/75

7/25/2019 Aldehyde Keton

7/75

7/25/2019 Aldehyde Keton

8/75

7/25/2019 Aldehyde Keton

9/75

7/25/2019 Aldehyde Keton

10/75

7/25/2019 Aldehyde Keton

11/75

EXAMPLE

7/25/2019 Aldehyde Keton

12/75

Physical Properties Molecules of aldehyde (or ketone) cannot hydrogen bond to

each other: They rely only on intermolecular dipole-dipole

interactions and therefore hae lo!er boiling points thanthe corresponding alcohols

"ldehydes and ketones can form hydrogen bonds !ith!ater and therefore lo! molecular !eight aldehydes andketones hae appreciable !ater solubility

7/25/2019 Aldehyde Keton

13/75

7/25/2019 Aldehyde Keton

14/75

7/25/2019 Aldehyde Keton

15/75

7/25/2019 Aldehyde Keton

16/75

7/25/2019 Aldehyde Keton

17/75

7/25/2019 Aldehyde Keton

18/75

EXAMPLE

7/25/2019 Aldehyde Keton

19/75

7/25/2019 Aldehyde Keton

20/75

7/25/2019 Aldehyde Keton

21/75

7/25/2019 Aldehyde Keton

22/75

7/25/2019 Aldehyde Keton

23/75

7/25/2019 Aldehyde Keton

24/75

7/25/2019 Aldehyde Keton

25/75

7/25/2019 Aldehyde Keton

26/75

7/25/2019 Aldehyde Keton

27/75

7/25/2019 Aldehyde Keton

28/75

7/25/2019 Aldehyde Keton

29/75

7/25/2019 Aldehyde Keton

30/75

" catalytic amount of cyanide helps to speed thereaction

7/25/2019 Aldehyde Keton

31/75

The cyano group can be hydroly#ed orreduced

$ydrolysis of a cyanohydrin produces an -hydro%ycarbo%ylic acid&eduction of a cyanohydrin produces a -

aminoalcohol

'

7/25/2019 Aldehyde Keton

32/75

7/25/2019 Aldehyde Keton

33/75

7/25/2019 Aldehyde Keton

34/75

7/25/2019 Aldehyde Keton

35/75

7/25/2019 Aldehyde Keton

36/75

7/25/2019 Aldehyde Keton

37/75

7/25/2019 Aldehyde Keton

38/75

7/25/2019 Aldehyde Keton

39/75

7/25/2019 Aldehyde Keton

40/75

7/25/2019 Aldehyde Keton

41/75

7/25/2019 Aldehyde Keton

42/75

7/25/2019 Aldehyde Keton

43/75

7/25/2019 Aldehyde Keton

44/75

7/25/2019 Aldehyde Keton

45/75

7/25/2019 Aldehyde Keton

46/75

7/25/2019 Aldehyde Keton

47/75

7/25/2019 Aldehyde Keton

48/75

7/25/2019 Aldehyde Keton

49/75

7/25/2019 Aldehyde Keton

50/75

7/25/2019 Aldehyde Keton

51/75

7/25/2019 Aldehyde Keton

52/75

7/25/2019 Aldehyde Keton

53/75

7/25/2019 Aldehyde Keton

54/75

7/25/2019 Aldehyde Keton

55/75

EXAMP

LE

7/25/2019 Aldehyde Keton

56/75

FORMATION OF HEMIACETAL

7/25/2019 Aldehyde Keton

57/75

7/25/2019 Aldehyde Keton

58/75

7/25/2019 Aldehyde Keton

59/75

7/25/2019 Aldehyde Keton

60/75

7/25/2019 Aldehyde Keton

61/75

EXAMPLE

7/25/2019 Aldehyde Keton

62/75

7/25/2019 Aldehyde Keton

63/75

7/25/2019 Aldehyde Keton

64/75

Additions to Unsatrated Aldehydes

7/25/2019 Aldehyde Keton

65/75

Additions to ,-Unsatrated Aldehydesand !etones a,b-nsaturated aldehydes and ketones can react by

simple (,*) or con+ugate (,) additionBoth the carbonyl carbon and the carbon are

electrophilic and can react !ith nucleophiles

.

/tronger nucleophiles such as 0rignard reagents faor ,*

7/25/2019 Aldehyde Keton

66/75

g p g gaddition !hereas !eaker nucleophiles such as cyanide oramines faor , addition

7/25/2019 Aldehyde Keton

67/75

7

1on+ugate "ddition of 2rganocopper &eagents

7/25/2019 Aldehyde Keton

68/75

1on+ugate "ddition of 2rganocopper &eagents2rganocopper reagents add almost e%clusiely in a

con+ugate manner to ,-unsaturated aldehydes andketones

3

7/25/2019 Aldehyde Keton

69/75

Michael "dditions

7/25/2019 Aldehyde Keton

70/75

Michael "dditions "ddition of an enolate to an ,-unsaturated carbonyl

compound usually occurs by con+ugate addition

This reaction is called a Michael addition

1hapter 7 74

7/25/2019 Aldehyde Keton

71/75

7/25/2019 Aldehyde Keton

72/75

7/25/2019 Aldehyde Keton

73/75

7/25/2019 Aldehyde Keton

74/75

7/25/2019 Aldehyde Keton

75/75