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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 𝜶 hydrogens around the triple bond whereas for the 2nd compound, there is no such 𝜶 Hydrogens generated around the newly formed double bond. Thus, cumulative diene is not formed.

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Most popular questions from this chapter

Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?

Draw the substitution product formed by each of the following SN2 reactions:

a. trans-1-iodo-4-ethylcyclohexane and methoxide ion

b. cis-1-chloro-3-methylcyclobutane and ethoxide ion

After a proton is removed from the OH group, which compound in each pair forms a cyclic ether more rapidly?

Draw the elimination products that are formed when 3-bromo-3-methyl-1-butene reacts with

Two elimination products are obtained from the following E2 reaction

a. What are the elimination products?

b. Which is formed in greater yield? (Hint:See Problem 91.)
See all solutions

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