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Lecture 10

CHEMК22200 Lecture 10: Handout 10(15)
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5 Pages
29 Views
Spring 2015

Department
Chemistry
Course Code
CHEM 22200
Professor
Joseph Piccirilli
Lecture
10

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Ar N N
The Sandmeyer
Reaction
-H2O
-N2
arenediazonium salt
Ar N NH2R N N -H2O
-N2
alkyldiazonium salt
R N NH2
R
N
N
N
N
N
N
N
N
Resonance structures stabilize the arenediazonium cation.
phenyl cation
harder to do compared to alkyldiazonium salt easier to do compared to areneldiazonium salt
Arenediazonium salts are stabilized by resonance
Ar N N
The Sandmeyer
Reaction
-H2O
-N2
arenediazonium salt
NH2
HONO
0-5oC
N3
Cu2O, Cu2+, H2O
CuBr
CuCl
CuCN
KI
(1) HBF4
(2) heat
H3PO2, H2O
OH
Br
Cl
CN
I
F
H
Ar N N
The Sandmeyer Reaction

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Description
Arenediazonium salts are stabilized by resonance Resonance structures stabilize the arenediazonium cation. N N N N N N N N arenediazonium salt alkyldiazonium salt Ar N NH H2O H2O 2 Ar N N R N NH 2 R N N harder to do compared to alkyldiazonium salt easier to do compared to areneldiazonium salt phenyl cation N2 N2 R The Sandmeyer Reaction
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