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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
- Propose 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_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_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
- Mechanism of azide synthesis: Step 1: Nucleophilic substitution of alkyl halide with sodium azide to form an alkyl azide. Step 2: Reduction of alkyl azide with a reducing agent such as sodium borohydride or lithium aluminum hydride to form an alkylamine. Mechanism of alkylation of ammonia: Step 1: The alkyl halide undergoes a nucleophilic substitution reaction with ammonia gas to form an intermediate alkylamine. Step 2: The intermediate alkylamine is deprotonated by the catalyst to form the final alkylamine.arrow_forwardWhen a student treated butanedioic acid with thionyl chloride, she was surprised to find that the product she obtained was an anhydride rather than an acyl chloride. Propose a mechanism to explain why she obtained an anhydride.arrow_forwardhow to synthesize 2-phenylclohexanone from cyclohexanone?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
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