In either acid or base, 3-cyclohexenone comes to equilibrium with 2-cyclohexenone: (a) Explain why the equilibrium favors
Question:
In either acid or base, 3-cyclohexenone comes to equilibrium with 2-cyclohexenone:
(a) Explain why the equilibrium favors the α,β-unsaturated ketone over its β,γ-unsaturated isomer.
(b) Give a mechanism for this reaction in aqueous NaOH.
(c) Give a mechanism for the same reaction in dilute aqueous H2SO4.
(d) Is the equilibrium constant for the analogous reaction of 4-methyl-3- cyclohexenone expected to be greater or smaller? Explain.
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a The equilibrium favors the aunsaturated isomer because it is conjugated Conjugation is a stabilizi...View the full answer
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