Carbonyl Compounds I

1
Carbonyl Compounds I
Reactions of Carboxylic Acids Their
Derivatives with Oxygen and Nitrogen Nucleophiles
2
(No Transcript)
3
(No Transcript)
4
(No Transcript)
5
(No Transcript)
6
(No Transcript)
7
(No Transcript)
8
(No Transcript)
9
(No Transcript)
10
Esters
11
Cyclic Esters
12
Amides
13
(No Transcript)
14
Acyl Chloride
CH3C(O)Cl ethanoyl chloride CH3CH2CH(CH3)CH2C(
O)Br 3-methylpentanoyl bromide
15
Acid anhydrides
ethanoic unhdride
CH3COCCH3 CH3COCH
ethanoic methanoic unhdride
16
The Structure of Carboxylic Acids
17
Carboxylic Acids, Esters and Amides have two
majors
Resonance contibutors
18
Physical Properties of Carbonyl Compounds
Amides gt carboxylic acids gt nitriles gtgt esters
acyl chlorides Aldhydes ketones
19
(No Transcript)
20
(No Transcript)
21
Reactivity Considerations
22

• Nu is wk base b. Nu is stronger c. Nu
  L.G
• than the leaving base than L.G
• group

K-1 gtgtK2 K2gtgtK-1
k-1 K2
23
Relative Reactivities of a Carboxylic Acid
Derivat
relative basicities of the leaving groups Cl- lt
-OC(O)R lt -OR -OH lt -NH2
24
(No Transcript)
25
(No Transcript)
26
(No Transcript)
27
(No Transcript)
28
(No Transcript)
29
General Mechanism For Nucleophlic Acyl
Substitution Reactions
30
Reactions of Acyl Halides
31
Reactions of Acyl Halides
32
(No Transcript)
33
(No Transcript)
34
(No Transcript)
35
Explain why only one amide is obtained from
reaction of acetyl chloride with a mixture of
ethylamine and pyridine.
36
Reactions of Acid Unhydrides
i.e. No reaction
37
Reactions of Acid Unhydrides
38
Reactions of Acid Unhydrides
39
Reactions of Esters
40
Reactions of Esters
41
(No Transcript)
42
Reactions of Esters
43
(No Transcript)
44
(No Transcript)
45
(No Transcript)
46
(No Transcript)
47
Acid-Catalyzed Ester Hydrolysis
48
(No Transcript)
49
(No Transcript)
50
(No Transcript)
51
basic solution
52
(No Transcript)
53
Reactions of Carboxylic Acids
54
Reactions of Carboxylic Acids
55
Reactions of Amides
56
Reactions of Amides
57
Reactions of Amides
58
(No Transcript)
59
(No Transcript)
60
(No Transcript)
61
(No Transcript)
62
The Gabrial Synthesis of Primary Amines
63
(No Transcript)
64
Hydrolysis of Nitriles
65
Hydrolysis of Nitriles
66
Hydrolysis of Nitriles
67
(No Transcript)
68
(No Transcript)
69
(No Transcript)
70
(No Transcript)
71
Synthesis of carboxylic Acid Derivatives
72
(No Transcript)
73
(No Transcript)
74
(No Transcript)
75
(No Transcript)
76
(No Transcript)
77
(No Transcript)
78
(No Transcript)
79
(No Transcript)
80
(No Transcript)
81
(No Transcript)
82
(No Transcript)
83
(No Transcript)
84
(No Transcript)
85
(No Transcript)