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Question

Which of the following is an example of rearrangement reaction?


A

CH3CH2CH2CH3 Alcl3−− CH3CH3|CHCH3

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B

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C

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D

None of these

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Solution

The correct options are
A

CH3CH2CH2CH3 Alcl3−− CH3CH3|CHCH3


B


C


In most of the organic reactions, the functional group of the substrate undergoes a structural change without affecting the C-skeleton of the molecule. But in some organic reactions atoms, groups (R or Ar), double bond, or functional group migrate within the molecule. Such types of reactions are called rearrangement or molecular rearrangement reactions. Migration of atoms or groups occurs usually from one adjacent atom to another within the same molecule.

The shift of M from X to Y is called 1,2-shift. If M is H, Me, or Ph it is called, 1,2-hydride shift, 1,2-methanide shift, or 1,2-phenyl shift, respectively. The rearrangement may take place through carbocation, carbanion, or free radical intermediates. The rearrangement through carbocation ¯¯¯e - deficient species is more common.

Now, you can see that in all options (a), (b) and (c) migration of atoms or group of atoms to another position within the molecule.


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