Concept explainers
The Perkin condensation is an aldol-type condensation in which an
(a) Outline the Perkin condensation that takes place when benzaldehyde reacts with propanoic anhydride in the presence of potassium propanoate.
(b) How would you use a Perkin condensation to prepare p-chlorocinnamic acid,
Want to see the full answer?
Check out a sample textbook solutionChapter 19 Solutions
Organic Chemistry
Additional Science Textbook Solutions
Living By Chemistry: First Edition Textbook
Chemistry: The Molecular Nature of Matter
Chemistry: Structure and Properties (2nd Edition)
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
Chemistry: A Molecular Approach (4th Edition)
Chemistry: An Introduction to General, Organic, and Biological Chemistry (12th Edition) - Standalone book
- The product of this reaction is a(n): H3CO OCH 3 cyanohydrin ketone aldehyde imine ester H3O+ productarrow_forwardComparing Hydration Products Using Two Different Methods Draw the product formed when CH3CH2C=CH is treated with each of the following sets of reagents: (a) H2O, H2SO4, HgSO4; and (b) R2BH, followed by H2O2, HO−.arrow_forwardbase 2 H3C H H3C OH heat H H3C + H₂O H 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. 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 Instructions X :OH H₂O: а کی H₂C H H₂C H Harrow_forward
- Can you draw the mechanism for the synthesis of cyclohexene from cyclohexanol through an acid-catalyzed dehydration reaction. Where Phosphoric acid donates a proton ((H^+)) to the hydroxyl group of cyclohexanol, forming a protonated cyclohexanol intermediate. • The protonated cyclohexanol undergoes dehydration, leading to the removal of a water molecule and the formation of cyclohexene. • The released proton combines with water to form hydronium ion (H3O+), regenerating the catalyst. The mechanism should illustrate the acid-catalyzed dehydration process, where phosphoric acid facilitates the removal of water from cyclohexanol, resulting in the formation of cyclohexene.arrow_forwardA graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. If this reaction could be accomplished using H2 and a nickel catalyst, would the product be optically active? Explain.arrow_forwardDraw the products of the diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + Δarrow_forward
- The formyl of an aldose is converted to which functional group when oxidized? alkoxide carbonyl carboxyl hydroxylarrow_forwardThe formyl of an aldose is converted to which functional group when oxidized? alkoxide carbonyl O hydroxyl carboxylarrow_forwardWhat explains why many aldehydes and ketones can undergo self-condensation reactions in basic conditions? The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon is an electrophile. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile. The oxygen of the carbonyl group can attack the carbon of the carbonyl group. Only esters can undergo self-condensation reactions.arrow_forward
- Explain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.arrow_forwardComplete the following synthesis by filling in the missing reactants, reagents, and products.• Boxes with sharp corners are structures; rounded corners are reagents (may be written or drawn).• Reagent boxes may hold multiple reagents/steps.arrow_forwardWhy must dehydration reactions of alcohols be carried out under acid catalysis? O 1) the hydroxide group is a poor leaving group and must be protonated to 1) generate a better leaving group. 2) the hydroxide group is a great leaving group and does not need to be protonated to generate a better leaving group. O 3) the acid isn't necessary for the reaction. O4) None of these are correct answers.arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning