Concept explainers
Interpretation:
Given that reaction of pyrrolidine enamine of cyclohexanone with but-2-ene-3-one followed by hydrolysis and base treatment yields the product shown. Each step with its mechanism is to be given.
Concept introduction:
The steps involved in the reaction are i) Michael addition of enamine to cyclohexanone ii) A proton transfer iii) Hydrolysis to remove the
To give:
The mechanism of each step involved in reacting pyrrolidine enamine of cyclohexanone with but-2-ene-3-one followed by hydrolysis and base treatment to produce the product shown.
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Chapter 23 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
- The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forwardComplete the following multistep syntheses by showing the major products and the reagents nessesary for each steparrow_forwardPropose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.arrow_forward
- Show how alkylation and acylation of enamines and lithium enolates are usedsynthetically. Give mechanisms for these reactions.arrow_forwardThe mechanism for acidic hydrolysis of a nitrile resembles the basic hydrolysis, exceptthat the nitrile is first protonated, activating it toward attack by a weak nucleophile (water).Under acidic conditions, the proton transfer (tautomerism) involves protonation on nitrogen followed by deprotonation on oxygen. Propose a mechanism for the acid-catalyzedhydrolysis of benzonitrile to benzamide.arrow_forward2-Ethyl-1-hexanol was needed for the synthesis of the sunscreen octyl p-methylcinnamate. Show how this alcohol could be synthesized (a) by an aldol condensation of butanal and (b) by a malonic ester synthesis starting with diethyl malonate.arrow_forward
- Please give the appropriate reagents to complete the following synthesis.arrow_forwardPropose a mechanism for the reaction of benzoic acid with oxalyl chloride. This mechanismbegins like the thionyl chloride reaction, to give a reactive mixed anhydride. Nucleophilicacyl substitution by chloride ion gives a tetrahedral intermediate that eliminates a leavinggroup, which then fragments into carbon dioxide, carbon monoxide, and chloride ion.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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