In an aldol condensation reaction, acetone and benzaldehyde are mixed in the presence of sodium hydroxide to produce dibenzalacetone. Does it matter whether the acetone is added first to the aq. NaOH solution then the benzaldehyde, or if the benzaldehyde is added first to the aq. NaOH solution, then the acetone? Explain

In an aldol condensation reaction, acetone and benzaldehyde are mixed in the presence of sodium hydroxide to produce dibenzalacetone. Does it matter whether the acetone is added first to the aq. NaOH solution then the benzaldehyde, or if the benzaldehyde is added first to the aq. NaOH solution, then the acetone? Explain

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter26: Aldol And Claisen Reactions

Section: Chapter Questions

Problem 19CTQ

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Which statement describes why aldol reactions with ketones are low yielding? A.Ketones do not have acidic protons. B.Ketones are too electron poor at the carbonyl carbon. C.Ketones can attack other ketones well but perform poorly in self-condensations. D.The product of a ketone addition to a ketone has considerable steric strain.
for the theroretical yield is the mol correct? also using the aldol condensation reaction in this portion are we using the aldol condensation reaction to synthesize acetophenone and para-methybenzaldehye. acetophenone 0.5 g, 4.2 mmol Para-methylbenzaldehyde 0.5 g, 4.2 mmol NaOH=0.18g = 4.5 mol Theroretical yield=0.93g =0.0519 mol Percent yield=76.8% Actual yield= 0.715 g Melting point observered= 93 degree Celsius Expected melting point =93-94.5 degree Celsius
Draw out the machanism for the aldol condensation of (2E,6E)-2,6-bis(4-ethylbenzylidene)cyclohexanone. (the reaction between cyclohexanone and 4-methoxybenzaldehyde)
There are other condensation reactions similar to the aldol and Claisen condensations:a. The Perkin condensation is the condensation of an aromatic aldehyde and acetic anhydride. Draw the product obtained from the following Perkincondensation: b. What compound is formed if water is added to the product of a Perkin condensation?c. The Knoevenagel condensation is the condensation of an aldehyde or a ketone that has no a-hydrogens and a compound such as diethyl malonatethat has an a-carbon flanked by two electron-withdrawing groups. Draw the product obtained from the following Knoevenagel condensation: d. What product is obtained when the product of a Knoevenagel condensation is heated in an aqueous acidic solution?
The aldol double condensation reaction is highly selective for formation of a single double condensation product. Explain why only one aldol condensation product is formed despite two carbonyl compounds being present for the reaction.
Using cyclopentanone as the reactant, show the product of a. acid-catalyzed keto–enol interconversion. b. an aldol addition. c. an aldol condensation.
Does it matter whether acetone is added first to the eq. NaOH solution then the benzaldehyde, or if the benzaldehyde is added first to the aq. NaOH solution, then the acetone in an aldol synthesis of dibenzalacetone
Which of the following compounds would you expect to undergo aldol self-condensation? Show the product of each successful reaction. (a) Trimethyl acetaldehyde (d) 3-Pentanone(b ) Cyclobutanone (e) Decanal(c) Benzophenone (diphenyl ketone) (f) 3-Phenyl-2-propenal
Give the structures of the aldol products that form when each of the following compounds or mixtures is treated with NaOH. The top three compounds are aldol dimerizations and require 2 moles of the reactant listed, while the two compounds on the bottom row are being used in a mixed aldol reaction. Butanal, Cyclopentanone, and Acetophenone (PhCOCH3) p-chlorobenzaldehyde and 2,2-dimethylcyclohexanone
Draw the product formed (after dehydration) in the crossed aldol condensation of phenylacetaldehyde (C6H5CH2CHO) with CH2(CO2Et)2 in the presence of sodium hydroxide.
What types of species are the electrophile and nucleophile in an aldol addition? 1. Nu: ester, E+: carbonyl 2. Nu: carbonyl, E+: carbonyl 3. Nu: carbonyl, E+: ester 4. Nu: ester, E+: ester
Your aldol condensation procedure calls for refluxing vanillin in acetone and NaOH for an hour. Whatmight happen if you didn’t heat the reaction, or heated it for too short a time? a) A mixture of aldol products and hydroxyketone intermediates would form.b) No reaction would occur, as the heat is needed to deprotonate the acetone.c) The reaction would still be successful.d) No reaction would occur, as the heat is needed to dissolve the NaOH.