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Primary:
R1H2C
R3
H2C
R2
R2
R3
+ R1
-cleavage
Secondary:
H2C
H2C
R3
H2C
R2
R2
H2C
R2
[R3 - H]
onium reaction
[R2 - H]
Aliphatic Amines
+.
O
Ar
C2H5
Ar
-cleavage
C2H5
CH3
+.
O
Ar
C2H5
CH3
C-O cleavage
Ar
CH3
+.
O
+.
Ar
C2H5
Ar
H
CH3
CH3
Secondary:
R
CH2
R(-H) +
O=CH2
H
onium reaction
CH3
- CH3
- CO
CH3
+ H2CO
C5H5+
Examples of Aromatic
Ether Cleavages
R2
R1
R2
+.
+.
R3
+ . OH
+ R1
-cleavage
R3
+O
OH
CH2
-C2H5
H-rearrangement
-CO
-CO
+CH3
H
O
If both alkyl groups can undergo the McLafferty rearrangement, the more
abundant product is due to reaction from the larger group. Also, the
product of two successive alkene eliminations usually appears as an
abundant ion.