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(a)
Interpretation:
The given compound is to be analyzed and the starting materials required for its synthesis using Claisen condensation are to be predicted. The possible Claisen condensation which would be a reasonable route to the desired product is to be decided.
Concept introduction:
The condensation reaction of two esters in presence of
(b)
Interpretation:
The given compound is to be analyzed and the starting materials required for its synthesis using Claisen condensation are to be predicted. The possible Claisen condensation which would be a reasonable route to the desired product is to be decided.
Concept Introduction:
The condensation reaction of two esters in presence of
(c)
Interpretation:
The given compound is to be analyzed and the starting materials required for its synthesis using Claisen condensation are to be predicted. The possible Claisen condensation which would be a reasonable route to the desired product is to be decided.
Concept Introduction:
The condensation reaction of two esters in presence of
(d)
Interpretation:
The given compound is to be analyzed and the starting materials required for its synthesis using Claisen condensation are to be predicted. The possible Claisen condensation which would be a reasonable route to the desired product is to be decided.
Concept Introduction:
The condensation reaction of two esters in presence of
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Chapter 22 Solutions
EBK ORGANIC CHEMISTRY
- Draw the possible enolate product(s) formed when the following carbonyl compounds are treated with one equivalent of lithium diisopropylamide. If more than one enolate product could arise, identify the most stable enolate by circling it.arrow_forwardExplain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.arrow_forwardCompound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives the following 1H NMR spectrum. Identify the compounds A and Carrow_forward
- Predict the products when each compound undergo Ozonolysis (a) (b) (c) , (d) (e)arrow_forwardShow how you would synthesize octanal from each compound. You may use any necessary reagents.(a) octan-1-olarrow_forwardThe 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) What product is formed by the Claisen rearrangement of compound Z? (b) Using what you have learned about ring-closing metathesis in Chapter 26, draw the product formed when the product in part (a) is treated with Grubbs catalyst. These two reactions are key steps in the synthesis of garsubellin A, a biologically active natural product that stimulates the synthesis of the neurotransmitter acetylcholine. Compounds of this sort may prove to be useful drugs for the treatment of neurodegenerative diseases such as Alzheimer’s disease.arrow_forward4.33 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.arrow_forwardPropose suitable reagents to accomplish the following transformations.arrow_forward
- Propose suitable reagents to accomplish the following transformations.arrow_forward(a) What product is formed by the Claisen rearrangement of compound Z? (b) Using what you have learned about ring-closing metathesis in Chapter 24, draw the product formed when the product in part (a) is treated with Grubbs catalyst. These two reactions are key steps in the synthesis of garsubellin A, a biologically active natural product that stimulates the synthesis of the neurotransmitter acetylcholine. Compounds of this sort may prove to be useful drugs for the treatment of neurodegenerative diseases such as Alzheimer's disease.arrow_forwardGive the structure of the product formed on reaction of ethyl acetoacetate with each of the following: (a) 1-Bromopentane and sodium ethoxide (b) Saponification (basic hydrolysis) and decarboxylation of the product in part (a) (c) Methyl iodide and the product in part (a) treated with sodium ethoxide (d) Saponification and decarboxylation of the product in part (c) (e) 1-Bromo-3-chloropropane and one equivalent of sodium ethoxide (f) Product in part (e) treated with a second equivalent of sodium ethoxide (g) Saponification and decarboxylation of the product in part (f) (h) Phenyl vinyl ketone and sodium ethoxide (i) Saponification and decarboxylation of the product in part (h)arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning