Concept explainers
Interpretation:
A mechanism for the formation of paraldehyde when three equivalents of acetaldehyde react in the presence of an acid catalyst is to be proposed.
Concept introduction:
The acid catalyst protonates an
To propose:
A mechanism for the formation of paraldehyde when three equivalents of acetaldehyde react in the presence of an acid catalyst.
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Chapter 19 Solutions
Organic Chemistry
- Isoamyl acetate (also known as isopentyl acetate) is an ester that is referred to as “banana flavor” due to its odor that resembles that of banana. It can be synthesized from isopentyl alcohol and acetic acid via nucleophilic acyl substitution mechanism. Propose a mechanism for the synthesis of isoamyl acetate from acetic acid and isoamyl alcohol.arrow_forwardPredict the products formed when cyclohexanone reacts with the following reagents. h) sodium acetylide, then mild H3O+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_forward
- The 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_forwardPropose a synthesis of the anti-inflammatory drug Fenclorac from phenylcyclohexane.arrow_forwardHow does propane synthesized from propanone? Show its mechanism.arrow_forward
- When 4-hydroxybutanoic acid is treated with an acid catalyst, it forms a lactone (a cyclic ester). Draw the structural formula of this lactone and propose a mechanism for its formationarrow_forwardAldehydes 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_forwardEthylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forward
- Claisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forwardWhich carbonyl groups in the anticancer drug Taxol will undergo nucleophilic addition, and which will undergo nucleophilic substitution?arrow_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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning