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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- The Meerwein-Ponndorf-Verley reaction involves reduction of a ketone by treatment with an excess of aluminum triisopropoxide, [(CH3)2CHO]3Al. The mechanism of the process is closely related to the Cannizzaro reaction in that a hydride ion acts as a leaving group. Propose a mechanism.arrow_forwardEthylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardWhen cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning