(a)
Interpretation:
The way by which alkylation or acylation of an enamine can be used to convert acetophenone into the given compound has to be shown.
Concept introduction:
Enamine:
An enamine is a compound where the lone pair of electrons in the nitrogen atom of
It is formed by the reaction of a
Hydrolysis of enamine: Under acidic conditions, enamine reacts with water to give corresponding ketone and secondary amine.
Here, the bond between nitrogen and the
(b)
Concept introduction:
Enamine:
An enamine is a compound where the lone pair of electrons in the nitrogen atom of
It is formed by the reaction of a ketone or aldehyde and a secondary amine under acidic conditions with the elimination of water molecule.
Hydrolysis of enamine: Under acidic conditions, enamine reacts with water to give corresponding ketone and secondary amine.
Here, the bond between nitrogen and the
(c)
Concept introduction:
Enamine:
An enamine is a compound where the lone pair of electrons in the nitrogen atom of
It is formed by the reaction of a ketone or aldehyde and a secondary amine under acidic conditions with the elimination of water molecule.
Hydrolysis of enamine: Under acidic conditions, enamine reacts with water to give corresponding ketone and secondary amine.
Here, the bond between nitrogen and the
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Chapter 19 Solutions
Organic Chemistry, Loose-leaf Version
- Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_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_forwardDraw out the reaction mechanism for cyclohexanol to cyclohexanone. Sodium hypochlorite oxidation of an alcohol to a ketone with the product being cyclohexanone.arrow_forward
- How to synthesize cyclohexylbenze from cyclohexanone?arrow_forwardBenzene + nitration, followed by bromination, then reduction of the nitro group to an amine, followed by diazonization, addition of copper I cyanide to the reaction and the product is O benzoyl nitrile O ortho-bromoaniline O para-bromo-nitrobenzene O 3,5-dibromnobenzonitrile O para-bromobenzyl bromidearrow_forwardShow how you would synthesize octanal from each compound. You may use any necessary reagents.ethyl octanoatearrow_forward
- Show how you would synthesize octanal from each compound. You may use any necessary reagents.octanoic acidarrow_forwardThe 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_forwardThe reagent diisobutylaluminum hydride (DIBALH) reduces esters to aldehydes. When nitriles are treated with DIBALH followed by mild acid hydrolysis, the product is also an aldehyde. Propose a mechanism for this reduction.arrow_forward
- Show how you would synthesize octanal from each compound. You may use any necessary reagents.oct-1-ynearrow_forwardStarting with cyclohexanone and ethanol as the only organic reagents, use any inorganic reagents to propose a synthesis for the target molecule.arrow_forwardUsing your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cydohexanediol. Show all required reagents and all molecules synthesized along the way.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning