Why is it that when alpha cleavage is being done on the right structure, the squiggly line is put on the top carbon? Why not in the same position as the first structure?

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Why is it that when alpha cleavage is being done on the right structure, the squiggly line is put on the top carbon? Why not in the same position as the first structure?

*]*
alpha-
cleavage
:
loss of CH₂CH₂
CH₂
+
=CH₂} {^~^
m/z 101
12-11 2,6-Dimethylheptan-4-ol. CoHoo has molecular weight 144 The highest mass pools at 126
alpha-
cleavage
H
m/z 87
loss of CH3
E-}
Transcribed Image Text:*]* alpha- cleavage : loss of CH₂CH₂ CH₂ + =CH₂} {^~^ m/z 101 12-11 2,6-Dimethylheptan-4-ol. CoHoo has molecular weight 144 The highest mass pools at 126 alpha- cleavage H m/z 87 loss of CH3 E-}
Expert Solution
Step 1

If you do the same for the same position as the first structure you may get the same structure as both will give same structure and generally α-cleavage is performed based on two main conditions that are 

1. Bulky radicals are preferred.

2. Stability of carbonation 

So in both case carbonation is stabilized by mesomeric effect (+M)  of oxygen and in 2nd molecule both +M of oxygen and hyperconjugation of 3α-H of CH3

 

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