Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 23.SE, Problem 55AP
Interpretation Introduction
Interpretation:
A mechanism for the acid catalyzed aldol condensation is to be given indicating the reactive nucleophile involved in the reaction.
Concept introduction:
To give:
A mechanism for the acid catalyzed aldol condensation is to be given indicating the reactive nucleophile involved in the reaction.
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2
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
H
2 CH3COOCH,CH3 C2H5O'K*/C2H5OH ---> CH3COCH,COOCH,CH3
[+]
Hofmann elimination
Clemmensen reduction
Claisen condensation
O Cannizzaro reaction
O Aldol condensation
2) An enolate attacks an aldehyde and the resulting product is subsequently protonated. W
type of reaction is this?
A) a Fischer esterification
B) an acid-catalyzed aldol condensation
C) a base-mediated aldol condensation
D) a Hell-Volhard-Zelinsky reaction
Chapter 23 Solutions
Organic Chemistry
Ch. 23.1 - Prob. 1PCh. 23.1 - Prob. 2PCh. 23.3 - Prob. 3PCh. 23.3 - Prob. 4PCh. 23.4 - Prob. 5PCh. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7PCh. 23.5 - Prob. 8PCh. 23.6 - Prob. 9PCh. 23.6 - What product would you Expect to obtain from base...
Ch. 23.7 - Show the products you would expect to obtain by...Ch. 23.7 - Prob. 12PCh. 23.8 - What product would you expect from the following...Ch. 23.9 - What product would you expect From the following...Ch. 23.9 - Prob. 15PCh. 23.10 - Prob. 16PCh. 23.10 - Prob. 17PCh. 23.10 - Prob. 18PCh. 23.11 - Prob. 19PCh. 23.11 - Show how you might use an enamine reaction to...Ch. 23.12 - Prob. 21PCh. 23.12 - How would you prepare the following compound using...Ch. 23.SE - Prob. 23VCCh. 23.SE - Prob. 24VCCh. 23.SE - Prob. 25VCCh. 23.SE - The following molecule was formed by a Robinson...Ch. 23.SE - Prob. 27MPCh. 23.SE - Prob. 28MPCh. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Knoevenagel condensation is a reaction involving...Ch. 23.SE - Azlactones are important starting materials used...Ch. 23.SE - Prob. 34MPCh. 23.SE - Isoleucine, another of the twenty amino acids...Ch. 23.SE - The first step in the citric acid cycle of food...Ch. 23.SE - Prob. 37MPCh. 23.SE - The Knoevenagel reaction is a carbonyl...Ch. 23.SE - The Darzens reaction invoIves a two-step,...Ch. 23.SE - The following reaction involves a hydrolysis...Ch. 23.SE - Prob. 41MPCh. 23.SE - Prob. 42MPCh. 23.SE - Prob. 43MPCh. 23.SE - Propose a mechanism for the following...Ch. 23.SE - Prob. 45MPCh. 23.SE - Prob. 46MPCh. 23.SE - Prob. 47MPCh. 23.SE - Prob. 48APCh. 23.SE - Prob. 49APCh. 23.SE - Prob. 50APCh. 23.SE - Prob. 51APCh. 23.SE - Prob. 52APCh. 23.SE - Prob. 53APCh. 23.SE - Prob. 54APCh. 23.SE - Prob. 55APCh. 23.SE - Prob. 56APCh. 23.SE - Prob. 57APCh. 23.SE - Prob. 58APCh. 23.SE - In the mixed Claisen reaction of cyclopentanone...Ch. 23.SE - Ethyl dimethylacetoacetate reacts instantly at...Ch. 23.SE - Prob. 61APCh. 23.SE - Prob. 62APCh. 23.SE - The so-called Wieland-Miescher ketone is a...Ch. 23.SE - Prob. 64APCh. 23.SE - Prob. 65APCh. 23.SE - Prob. 66APCh. 23.SE - What condensation products would you expect to...Ch. 23.SE - The following reactions are unlikely to provide...Ch. 23.SE - Fill in the missing reagents a-h in the following...Ch. 23.SE - Prob. 70APCh. 23.SE - Prob. 71APCh. 23.SE - Prob. 72APCh. 23.SE - Prob. 73AP
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- Provide reasonable mechanism for each step in the following reaction. First step is keto-Enol. Second step is acid catalyzed aldol reaction.arrow_forwardAcetal formation must be catalyzed by an acid. Explain why it cannot be catalyzed by CH3O-.arrow_forwardUnder basic conditions, in nucleophilic acyl substitution, O protonation of the carbonyl group is followed by nucleophilic attack. loss of the leaving group is followed by formation of an acylium ion. an SN2 mechanism is followed. the nucleophile must be a weaker base than the leaving group. O nucleophilic addition to the carbonyl is followed by loss of a leaving group.arrow_forward
- base 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_forwardIllustrate detailed mechanism for below attempted aldol reactionarrow_forwardCan you assist with the complete stepwise reaction mechanism for the following Aldol condensation reaction. curved arrows to show direction of electron flow.arrow_forward
- An aldol addition can be catalyzed by acids as well as by bases. Propose a mechanism for the acid-catalyzed aldol addition of propanal.arrow_forwardSubject: chemistryarrow_forwardThe Knoevenagel condensation reaction is a variant of the aldol reaction. A major drawback of the aldol reaction is self-aldehyde condensation. Identify the starting material in the Knoevenagel reaction that suppresses self-condensation and explainyour choice.arrow_forward
- Draw the product.arrow_forward16. Draw the structure of the aldol self-condensation (followed by dehydration) product for each of the following compounds. If a compound does not undergo aldol self-condensation, explain why it does not. a) || CH3CHCH₂CH T CH₂ b)arrow_forwardbase H3C H OH heat H + 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. In the mixed aldol reaction, the best results are obtained when one of the partners does not have an a-hydrogen. It cannot form an enolate anion and can therefore not undergo self-reaction. The enolizable aldehyde is added slowly to a basic solution of the first aldehyde so that the mixed product is preferentially formed. 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.…arrow_forward
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