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In crossed aldol condensation，in order to avoid unwanted product mixture，the compound without alpha hydrogen like benzaldehyde can be a good choice. Why？？？does it means that two enolate will produce unwanted product mixture？ 1. what is unwanted product mixture ？ 2. and what is wanted product

In crossed aldol condensation，in order to avoid unwanted product mixture，the compound without alpha hydrogen like benzaldehyde can be a good choice. Why？？？does it means that two enolate will produce unwanted product mixture？ 1. what is unwanted product mixture ？ 2. and what is wanted product

Chemistry
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
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In crossed aldol condensation，in order to avoid unwanted product mixture，the compound without alpha hydrogen like benzaldehyde can be a good choice. Why？？？does it means that two enolate will produce unwanted product mixture？ 1. what is unwanted product mixture ？ 2. and what is wanted product？
H olate H3 C-CH3 H ate H OH -utanal) nzaldehyde H H H H-C-CH3 C-C-H H- H OH is usually exothermic, driving the condensation to completion. The base- catalyzed dehydration of 3-hydroxybutanal is shown in Equation 2. H C -CH3 H H HO H C-C-H H enolate ion OH O H -C-CH3 H OH H O H H-C-CH3 C-C-H + TOH H H aldol (3-hydroxybutanal) A crossed aldol condensation is an aldol condensation in which one aldehyde or ketone adds to the carbonyl group of a different compound. The compounds used in a crossed aldol condensation must be carefully selected to avoid unwanted product mixtures. Crossed aldol condensations are most effective if only one of the reactants can form an enolate ion and the other reactant is particularly electrophilic toward enolates. Benzaldehyde is an excellent reagent for crossed aldols because it has no a-hydrogens, so it cannot form an enolate. The base-catalyzed condensation of acetaldehyde with benzaldehyde is shown in Equation 3. H CH3 H H dehydrated OH H-C- (Eq. 1) C-C-H H aldol + OH (Eq. 2) + OH
Transcribed Image Text:H olate H3 C-CH3 H ate H OH -utanal) nzaldehyde H H H H-C-CH3 C-C-H H- H OH is usually exothermic, driving the condensation to completion. The base- catalyzed dehydration of 3-hydroxybutanal is shown in Equation 2. H C -CH3 H H HO H C-C-H H enolate ion OH O H -C-CH3 H OH H O H H-C-CH3 C-C-H + TOH H H aldol (3-hydroxybutanal) A crossed aldol condensation is an aldol condensation in which one aldehyde or ketone adds to the carbonyl group of a different compound. The compounds used in a crossed aldol condensation must be carefully selected to avoid unwanted product mixtures. Crossed aldol condensations are most effective if only one of the reactants can form an enolate ion and the other reactant is particularly electrophilic toward enolates. Benzaldehyde is an excellent reagent for crossed aldols because it has no a-hydrogens, so it cannot form an enolate. The base-catalyzed condensation of acetaldehyde with benzaldehyde is shown in Equation 3. H CH3 H H dehydrated OH H-C- (Eq. 1) C-C-H H aldol + OH (Eq. 2) + OH
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