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a) CH3CO2Et + CH3CH2CO2Et
Interpretation:
The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction are to be given.
Concept introduction:
The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.
To give:
The structures of the possible products, indicating predominant product if any, when ethylacetate and ethyl propionate undergo Claisen condensation reaction.
b) C6H5CO2Et + C6H5CH2CO2Et
Interpretation:
The structures of the possible products, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction are to be given.
Concept introduction:
The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.
To give:
The structure of the possible product, indicating predominant product if any, when ethylbenzoyate and ethylphenylacetate undergo Claisen condensation reaction.
c) EtOCO2Et + cyclohexanone
Interpretation:
The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction are to be given.
Concept introduction:
The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.
To give:
The structures of the possible products, indicating predominant product if any, when ethoxyethylformate and cyclohexanone undergo Claisen condensation reaction.
d) C6H5CHO + CH3CH2Et
Interpretation:
The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylformate undergo Claisen condensation reaction are to be given.
Concept introduction:
The Claisen condensation reaction involves a reversible condensation between two molecules of an ester that has α-hydrogen atoms in the presence of one equivalent of a base like sodium ethoxide. The product obtained is a β-keto ester. In the reaction an alcohol molecule is eliminated and the product has an acyl group of one of the reactant molecule attached to the α-carbon of the second molecule.
To give:
The structures of the possible products, indicating predominant product if any, when benzaldehyde and ethylacetate undergo Claisen condensation reaction.
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Chapter 23 Solutions
Organic Chemistry
- The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.arrow_forwardIf phenoxide ion is allowed to react with 1-bromopentane, pentyl phenyl ether is obtained. However, if cyclohexane is used as the alkyl halide, the major products are phenol and cyclohexene. Explain how these products were formed.arrow_forwardWhen 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1- butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for 70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium propoxide were the base? base Br A. Less than 45% B. C. 45% Between 45% and 70% D. More than 70%arrow_forward
- Diphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?arrow_forwardPropose a series of reactions that would convert the provided starting material into the given product. The synthesis will take more than one step. For each reaction you use, show the reagents you would use and the product of that step. In each step, your desired product should be formed as the major product. Assume chiral products are formed as racemic mixtures. Your reactions should give the correct diastereomer. All carbons in the final products must come from the provided starting materials. In addition to the provided starting materials, you may use any reagents we have discussed. Hint, you’ll need to convert the starting materials into functional groups that you can connect together. I need help with this practice problem, thank you!arrow_forwardThe following are intermediate products in the stepwise synthesis of compound 1 from benzene. Give the correct sequence of reactions with the appropriate reagents that will lead to the correct intermediate products and final product.arrow_forward
- single reaction sequence: a certain ketone undergoes alkylation to give new ketone, when reacted with a base and then an alkylating agent, 1-bromopropane. What is the structure of the final ketone product?arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardPredicts the major products for the following reaction.arrow_forward
- Draw the structure(s) of the major organic product(s), including counterions, of the following reaction. HBr + NH₂arrow_forwardPropose a series of reactions that would convert the provided starting material into the given product. The synthesis will take more than one step. For each reaction you use, show the reagents you would use and the product of that step. In each step, your desired product should be formed as the major product. Assume chiral products are formed as racemic mixtures. Your reactions should give the correct diastereomer. In addition to the provided starting material, you may use any other organic compound as well as any reagents we have discussed. Could someone please help me with this practice problem? Thank you!arrow_forwardDraw the major organic product obtained by reaction of benzoyl chloride with dimethylamine, (CH3)2NH.arrow_forward
- Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
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