Interpretation:
The mechanism for the given acid-catalyzed aldol reaction and the dehydration of the resulting aldol product has to be proposed.
Concept Introduction:
The nucleophilic addition of the enolate anion of one
The dehydration of the Aldol product (β-hydroxy aldehyde or ketone) occurs under acidic or basic conditions and form α,β-unsaturated aldehyde or ketone.
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Chapter 19 Solutions
OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- What is the product formed when each dicarbonyl compound undergoes an intramolecular aldol reaction, followed by dehydration.arrow_forwardDraw the product formed when each dicarbonyl compound undergoes an intramolecular aldol reaction followed by dehydration, when possible.arrow_forwardPropose an appropriate intermediate for the following reactionarrow_forward
- Choose the best sequence of reagents to synthesize the indicated compound.arrow_forward2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O Harrow_forwardBenzalacetone is a side product formed in the aldol condensation of dibenzalacetone. Show the reaction mechanism of how this side product, Benzalacetone, is formed.arrow_forward
- When cyclohexanone is heated in the presence of a large amount of acetone cyanohydrin and a small amount of base, cyclohexanone cyanohydrin and acetone are formed. Propose a mechanism.arrow_forwardPropose a mechanism for the following acetal formation and acetal deprotection.arrow_forwardIsoamyl 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_forward
- Show how to prepare a,b-unsaturated aldehyde by an aldol reaction followed by dehydration of the aldol product.arrow_forwardProvide reasonable mechanism for each step in the following reaction. First step is keto-Enol. Second step is acid catalyzed aldol reaction.arrow_forwardAcetic acid has been mixed with isoamyl alcohol to produce isoamyl acetate giving off a banana smell. Propose a reaction mechanism for this reaction.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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