
(a)
Interpretation:
For the rearrangement reaction of the given compound, the mechanism should be drawn, the type of Sigmatropic rearrangement should be identified and the reason for completion of reaction should be explained.
Concept introduction:
- Sigmatropic rearrangement reaction is a pericyclic reaction of polyenes (π-system), in which one σ-bond is formed and another σ-bond is broken and remaining π-bonds are shifting their positions. Thereby the transition state is cyclic. The mechanism of rearrangement is represented by using curved arrows.
- The Sigmatropic rearrangement reaction is represented by using two numbers in the brackets. The numbers represent the numbers of atoms separating the σ-bond which is breaking and the σ-bond which is forming.
- Three membered rings are highly unstable as compared to seven membered rings because the angle strain is increase with decrease in the bond angle.
(b)
Interpretation:
For the rearrangement reaction of the given compound, the mechanism should be drawn, the type of Sigmatropic rearrangement should be identified and the reason for completion of reaction should be explained.
Concept introduction:
- Sigmatropic rearrangement reaction is a pericyclic reaction of polyenes (π-system), in which one σ-bond is formed and another σ-bond is broken and remaining π-bonds are shifting their positions. Thereby the transition state is cyclic. The mechanism of rearrangement is represented by using curved arrows.
- The Sigmatropic rearrangement reaction is represented by using two numbers in the brackets. The numbers represent the numbers of atoms separating the σ-bond which is breaking and the σ-bond which is forming.
- Three membered rings are highly unstable as compared to seven membered rings because the angle strain is increase with decrease in the bond angle.
(c)
Interpretation:
For the rearrangement reaction of the given compound, the mechanism should be drawn, the type of Sigmatropic rearrangement should be identified and the reason for completion of reaction should be explained.
Concept introduction:
- Sigmatropic rearrangement reaction is a pericyclic reaction of polyenes (π-system), in which one σ-bond is formed and another σ-bond is broken and remaining π-bonds are shifting their positions. Thereby the transition state is cyclic. The mechanism of rearrangement is represented by using curved arrows.
- The Sigmatropic rearrangement reaction is represented by using two numbers in the brackets. The numbers represent the numbers of atoms separating the σ-bond which is breaking and the σ-bond which is forming.
- Three membered rings are highly unstable as compared to seven membered rings because the angle strain is increase with decrease in the bond angle.

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Chapter 16 Solutions
Organic Chemistry, Third Edition Binder Ready Version
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