Reactions of carbonyl Compounds with carbon and

1
Chapter 17
Reactions of carbonyl Compounds with carbon
and Hydrogen Nucleophiles Reactions of Aldhydes
and Ketones with Oxygen and Nitrogen
Nucleophiles Reactions of a b Unsaturated
Carbonyl Compounds
2
(No Transcript)
3
(No Transcript)
4
(No Transcript)
5
Nomenclature Aldhyde
6
Nomenclature Aldhyde
7
Nomenclature Aldhyde
8
(No Transcript)
9
(No Transcript)
10
(No Transcript)
11
(No Transcript)
12
Nomenclature ketones
13
(No Transcript)
14
Nomenclature Ketones
15
Nomenclature Ketones
16
Nomenclature Ketones
17
Nomenclature Ketones
18
(No Transcript)
19
(No Transcript)
20
(No Transcript)
21
(No Transcript)
22
(No Transcript)
23
Reactivity Considerations
Recall
24
(No Transcript)
25
Strong nucleophile does not need acid catalyst
26
Weak nucleophile needs acid catalyst
27
(No Transcript)
28
When the attacking atom of the nucleophile has a
a nonbonding Pair
29
Addition of Carbon Nucleophiles
30
Addition of Carbon Nucleophiles
31
Addition of Carbon Nucleophiles
32
Addition of Carbon Nucleophiles
33
Addition of Carbon Nucleophiles Acetylide ions
Alkynes can also produce R- as nucleophile
34
Alkynes can also produce R- as nucleophile
35
(No Transcript)
36
(No Transcript)
37
(No Transcript)
38
Addition of Hydride Ion
39
Addition of Hydride Ion
NaBH4 sodium boron hydride (reducing agent)
40
Reactions of Carbonyl Compounds That Having a
Leaving groups with Grignard Reagents and
Hydride ion Donners
41
Reactions of Carbonyl Compounds That Having a
Leaving groups with Grignard Reagents and
Hydride ion Donners
42
Reactions With a Hydride Ion Donor
LiAlH4 lithium aluminum hydride
source of H-
43
Reactions With a Hydride Ion Donor
44
Reactions With a Hydride Ion Donor
45
(No Transcript)
46
(No Transcript)
47
(No Transcript)
48
Acyl chlorides like esters and carboxylic acids,
undergo Two successive additions of hydride ion
when treated With LiAlH4
49
(No Transcript)
50
(No Transcript)
51
(No Transcript)
52
(No Transcript)
53
(No Transcript)
54
Addition of Nitrogen Nucleophiles
Addition of Ammonia, primary amines, and other
ammonia derivatives, such as hydroxylamine
H2NOH, Hydrazine H2NNH2, semicarbazide
H2NNHCONH2, and primary amines
55
Bonding in Imine
56
(No Transcript)
57
(No Transcript)
58
Nucleophilic Addition-Elimination Reaction
59
Dependance of the reaction Of acetone with H2NOH
60
(No Transcript)
61
Imine hydrolysis is necessary step in the
conversion of a nitrile to a ketone
62
Addition of secondary amine
63
(No Transcript)
64
In an aqueous acidic solution, an amine is
hydrolyzed back to the carbonyl compound and
secondary amine
65
Addition of ammonia and Hydrogen Reductive
ammonia
66
Addition of ammonia and Hydrogen Reductive
ammonia
67
(No Transcript)
68
(No Transcript)
69
Addition of Oxygen Nucleophiles
addition of H2O
70
Addition of Oxygen Nucleophiles addition of H2O
initial 100

0
Finial
71
(No Transcript)
72
(No Transcript)
73
(No Transcript)
74
If the amount of hydrate formed from reaction of
acetone with water is too small to detect, how
do we know that the reaction is even occurred?
75
Addition of Alcohol
76
Addition of Alcohol
77
Addition of Alcohol
78
Addition of Alcohol
79
Addition of Alcohol Protecting Groups
80
Addition of Alcohol Protecting Groups
81
Addition of Alcohol Protecting Groups
82
Addition of Sulfur Nucleophiles
83
(No Transcript)
84
The Wittig Reaction
85
The Wittig Reaction
86
The Wittig Reaction
87
The Wittig Reaction
88
The Wittig Reaction
89
Stereochemistry of Nucleophilic Addition
Reactions RE SI Faces
90
(No Transcript)
91
(No Transcript)
92
(No Transcript)
93
(No Transcript)
94
(No Transcript)
95
(No Transcript)
96
(No Transcript)
97
(No Transcript)