Cinnamaldehyde may be synthesized through aldol condensation reaction of two aldehydes Q and R as shown below. 10% NaOH add R slowly T 5°C heat (-H20) Cinnamaldehyde Suggest structures for aldehydes Q and R. Identify which one will form the enolate ion and draw the structure (both resonances). а. b. Show the nucleophilic attack by the enolate on the other aldehyde and draw the structure of the B-hydroxyketone T produced. Show the formation of the a,ß-unsaturated ketone when a molecule of water is lost in the dehydration step. с.

Cinnamaldehyde may be synthesized through aldol condensation reaction of two aldehydes Q and R as shown below. 10% NaOH add R slowly T 5°C heat (-H20) Cinnamaldehyde Suggest structures for aldehydes Q and R. Identify which one will form the enolate ion and draw the structure (both resonances). а. b. Show the nucleophilic attack by the enolate on the other aldehyde and draw the structure of the B-hydroxyketone T produced. Show the formation of the a,ß-unsaturated ketone when a molecule of water is lost in the dehydration step. с.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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20. Provide the reactants and reaction conditions necessary for the following transformations. Stereochemistry and regiochemistry may be important. a. b. C. d. type: Oxidative cleavage type: Fisher esterification type: Acetal formation type: Aldol condensation TSOH OH + CO2 + H2O & volon
B. Dieckmann Condensations Just as there can be intramolecular Aldol condensations, so can there be intramolecular Claisen condensations. These are called Dieckmann condensations. 1) Identify all the a hydrogens in the diester shown. Draw the enolate anion(s) that form when the hydrogen(s) is/are removed. H3CH₂CO OCH₂CH3 2) Draw a mechanism and provide the product(s) formed when the anion(s) attack(s) the other carbonyl carbon in the molecule. All electron movement must be shown with arrows.
21.3 Aldol Reactions Provide the conditions necessary in the reaction below. MeO H H3O* NaOH H₂O, heat H₂O NaOH H₂O MeO 'H OMe
2. When the following pair of reactants are combined in the presence of a basic catalyst, a number of aldol addition products are possible). NaOH/H₂O A CH3 a. b. C. H₂C Draw the structure for the enolate ion (show both of the relevant resonance structures). Draw the structures for all possible aldol addition products (also show the enolate ion and electrophilic carbonyl compound responsible for each product). For each of the aldol addition products predicted in part b, draw the structures for all of the corresponding aldol condensation products after loss of water (if E/Z isomers are possible, show both isomers)
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4.Which is the most thermodynamically stable product of the following aldol condensation reaction? NaOH H. Me `Me EtOH а. Е, Z b. Е, E с. Z, E d. Z,Z