Concept explainers
a)
Interpretation:
Whether trimethylacetaldehyde undergoes aldol self-condensation reaction or not is to be stated. The product formed, if the reaction is successful, is also to be shown.
Concept introduction:
To state:
Whether trimethylacetaldehyde undergoes aldol self-condensation reaction or not.
To show:
The product formed, if the reaction is successful.
Answer to Problem 48AP
Trimethylacetaldehyde does not undergo aldol self-condensation reaction. The reaction is not successful.
Explanation of Solution
The requirement of aldol reaction is the aldehyde or ketone should have α-hydrogen atom. Trimethylacetaldehyde does not possess α-hydrogen atom. Hence the reaction is not successful.
Trimethylacetaldehyde does not undergo aldol self-condensation reaction. The reaction is not successful.
b)
Interpretation:
Whether cyclobutanone undergoes aldol self-condensation reaction or not is to be stated. The product formed, if the reaction is successful, is also to be shown.
Concept introduction:
Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.
To state:
Whether cyclobutanone undergoes aldol self-condensation reaction or not.
To show:
The product formed, if the reaction is successful.
Answer to Problem 48AP
Cyclobutanone undergoes aldol self-condensation reaction. The product formed is
Explanation of Solution
The requirement of aldol reaction is the aldehyde or ketone should have α-hydrogen atom. Cyclobutanone has α-hydrogen atoms. Hence the reaction is successful. Two molecules of cyclobutanone condense in the presence of a base to yield an aldol which dehydrates to give α, β-unsaturated ketone.
Cyclobutanone undergoes aldol self-condensation reaction. The product formed is
c)
Interpretation:
Whether benzophenone undergoes aldol self-condensation reaction or not is to be stated. The product formed, if the reaction is successful, is also to be shown.
Concept introduction:
Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.
To state:
Whether benzophenone undergoes aldol self-condensation reaction or not.
To show:
The product formed, if the reaction is successful.
Answer to Problem 48AP
Benzophenone does not undergo self aldol condensation reaction. The reaction is not successful.
Explanation of Solution
The requirement of aldol reaction is the aldehyde or ketone should have α-hydrogen atom. Benzophenone does not possess α-hydrogen atom. Hence the reaction is not successful.
Benzophenone does not undergo self aldol condensation reaction. Theb reaction is not successful.
d)
Interpretation:
Whether 3-pentanone undergoes aldol self-condensation reaction or not is to be stated. The product formed, if the reaction is successful, is also to be shown.
Concept introduction:
Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.
To state:
Whether 3-pentanone undergoes aldol self-condensation reaction or not.
To show:
The product formed, if the reaction is successful.
Answer to Problem 48AP
3-pentanone undergoes aldol self-condensation reaction. The product formed is
Explanation of Solution
The requirement of aldol reaction is the aldehyde or ketone should have α-hydrogen atom. 3-Pentanone has α-hydrogen atom. Hence the reaction is successful. Two molecules of 3-pentanone condense in the presence of a base to yield an aldol which dehydrates to give the α, β-unsaturated ketone.
3-pentanone undergoes aldol self-condensation reaction. The product formed is
e)
Interpretation:
Whether decanal undergoes aldol self-condensation reaction or not is to be stated. The product formed, if the reaction is successful, is also to be shown.
Concept introduction:
Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.
To state:
Whether decanal undergoes aldol self-condensation reaction or not.
To show:
The product formed, if the reaction is successful.
Answer to Problem 48AP
Decanal undergoes aldol self-condensation reaction. The product formed is
Explanation of Solution
The requirement of aldol reaction is the aldehyde or ketone should have α-hydrogen atom. Decanal has α-hydrogen atom. Hence the reaction is successful. Two molecules of decanal condense in the presence of a base to yield an aldol which dehydrates to give an α, β-unsaturated aldehyde.
Decanal undergoes aldol self-condensation reaction. The product formed is
f)
Interpretation:
Whether 3-phenyl-2-propenal undergoes aldol self-condensation reaction or not is to be stated. The product formed, if the reaction is successful, is also to be shown.
Concept introduction:
Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.
To state:
Whether 3-phenyl-2-propenal undergoes aldol self-condensation reaction or not.
To show:
The product formed, if the reaction is successful.
Answer to Problem 48AP
3-Phenyl-2-propenal does not undergo aldol self-condensation reaction. The reaction is not successful.
Explanation of Solution
The requirement of aldol reaction is the aldehyde or ketone should have α-hydrogen atom. 3-Phenyl-2-propenal does not possess α-hydrogen atom. Hence the reaction is not successful.
3-Phenyl-2-propenal does not undergo aldol self-condensation reaction. The reaction is not successful.
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Chapter 23 Solutions
Organic Chemistry
- The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forwardShow how you would synthesize octanal from each compound. You may use any necessary reagents.(a) octan-1-olarrow_forward4. Which of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate © Ethyl 2-methylbutanoate (b) Ethyl 3-methylbutanoate (d) Ethyl 2,2-dimethylpropanoatearrow_forward
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- The following questions pertain to the esters shown and behavior under conditions of the Claisen condensation.(a) Two of these esters are converted to β-keto esters in good yield on treatment with sodium ethoxide and subsequent acidification of the reaction mixture. Which two are these? Write the structure of the Claisen condensation product of each one. (b) One ester is capable of being converted to a β-keto ester on treatment with sodium ethoxide, but the amount of β-keto ester that can be isolated after acidification of the reaction mixture is quite small. Which ester is this? (c) One ester is incapable of reaction under conditions of the Claisen condensation. Which one? Why?arrow_forward(a) Draw a stepwise mechanism for the reaction of ethyl hexa-2,4-dienoate with diethyl oxalate in the presence of base. (b) How does your mechanism explain why a new carbon–carbon bond forms on C6? (c) Why is this reaction an example of a crossed Claisen reaction?arrow_forward(a) p-Nitrobenzaldehyde is reactive toward nucleophilic additions than p- more methoxybenzaldehyde. Draw both of the molecular structures and explain the observation. (b) Cyclohexanone forms a cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not. Draw both of the molecular structures and explain the observation.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning