Concept explainers
Interpretation:
A mechanism for the reversible equilibrium isomerization of 2-substituted-2-cyclopentanones to 5-substituted-2-cyclopentanones is to be proposed.
Concept introduction:
The steps involved in the reversible equilibrium isomerization of 2-substituted-2-cyclopentanones to 5-substituted-2-cyclopentanones are i) abstraction of a proton from the γ-carbon to form a resonance stabilized enolate ion ii) Protonation at the α- carbon iii) Abstraction of a proton from other α- carbon to form a different resonance stabilized enolate ion iv) Protonation of the γ- carbon.
To propose
A mechanism for the reversible equilibrium isomerization of 2-substituted-2-cyclopentanones to 5-substituted-2-cyclopentanones.
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Chapter 22 Solutions
Organic Chemistry
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- Treatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.arrow_forwardEthylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardCyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. Propose a structural formula for each intermediate compound.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning