Review Of Organic Chemistry Page 16
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34Organic Chemistry I Review: Highlights of Key Reactions, Mechanisms, and Principles
16
Ch. 15 Conjugated Systems
The General Stabilization Effect of Conjugation (Section 15.1, 2, 3, 8, 9)
Conjugated
Isolated
(more stable)
(less
Notes:
stable)
1
Cations
2
Radicals
3
Anions
4
Dienes
5
Ethers
An N or O next to a double bond becomes
2
3
sp
, not sp
!!
O
2
3
sp
. An isolated N or O is sp
3
sp
O
6
Amines
2
H
sp
N
N
3
sp
H
7
Esters
O
O
O
O
3
sp
2
sp
8
Amides
Very special, chapter 23, all of biochemistry,
O
O
2
sp
H
proteins, enzymes, etc.
N
N
3
sp
H
9
Oxyanions
Very special, chapter 21
O
O
(Carboxylates)
3
sp
O
O
2
sp
10 Carbanions
Very special, chapter 22
O
O
2
sp
(Enolates)
3
sp
11 Aromatics
Very special, chapters 16 + 17
2
Conjugation: Anything that is or can be sp
hybridized is stabilized when next to π bonds.
• oxygens, nitrogens, cations, radicals, and anions
Notes:
2
2
1. Any atom that can be sp
will be sp
when next to a double bond
2
2. “Conjugation” is when sp
centers are joined in an uninterrupted series of 3 or more, such that
an uninterrupted series of p-orbitals is possible
2
3. Any sp
center has one p orbital
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