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Chapter 9: Q50P (page 436)

Why is a cumulated diene not formed in the reaction shown below?

Short Answer

Expert verified

Cumulative diene is not formed due to the instability in its transition state.

Step by step solution

01

Reason for not forming cumulative diene

The above reaction proceeds through E2 elimination reaction which has an alkyl like transition state.

Alkyl like transition state get stabilized through the no of alpha Hydrogens attached to the unsaturated bond. For the 1st one, the compound has 6 饾湺 hydrogens around the triple bond whereas for the 2nd compound, there is no such 饾湺 Hydrogens generated around the newly formed double bond. Thus, cumulative diene is not formed.

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