What is the product of a [1,3] -sigmatropic shift in the following compound?

C) The compound shown cannot undergo a [1,3]-sigmatropic shift.

Question

What is the product of a  [1,3] -sigmatropic shift in the following compound?

C) The compound shown cannot undergo a [1,3]-sigmatropic shift.

Quizplus · Accepted Answer

The [1,3]-sigmatropic shift involves the migration of a group from one carbon to an adjacent carbon with the concomitant breaking and forming of bonds. In the given compound, the methyl group (-CH3) can migrate from the carbon marked with an asterisk to the adjacent carbon marked with a double bond. This results in the formation of a new double bond between the two carbons and the breaking of the double bond between the other two carbons. The resulting compound is represented by option B, which has a new double bond between the second and third carbons from the left.

What Is the Product of a [1,3] -Sigmatropic Shift