(a)
Interpretation:
The distribution of oxygen-18 in the products obtained from hydrolysis of ethyl benzoate labeled in the ethoxy oxygen in aqueous sodium hydroxide has to be given.
Concept introduction:
Ester Hydrolysis: Ester hydrolysis can be caused by acid and base.
Saponification: Ester hydrolysis taking place in presence of base such as
Acid-catalyzed hydrolysis: In presence of strong acid such as
(b)
Interpretation:
The distribution of oxygen-18 in the products obtained from hydrolysis of ethyl benzoate labeled in the ethoxy oxygen in aqueous sodium hydroxide has to be given.
Concept introduction:
Ester Hydrolysis: Ester hydrolysis can be caused by acid and base.
Saponification: Ester hydrolysis taking place in presence of base such as
Acid-catalysed hydrolysis: In presence of strong acid such as
(c)
Interpretation:
The distribution of oxygen-18 in the products obtained from hydrolysis of ethyl benzoate labeled in the ethoxy oxygen in the reaction of tert-butyl ester in
Concept introduction:
Ester Hydrolysis: Ester hydrolysis can be caused by acid and base.
Saponification: Ester hydrolysis taking place in presence of base such as
Acid-catalysed hydrolysis: In presence of strong acid such as
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Chapter 18 Solutions
Organic Chemistry
- Write a mechanism for the formation of cyclic ketal under acid catalysis in benzene. The catalysis is p-toluenesulfonic acid.arrow_forwardDraw a complete arrow pushing mechanism for the specific Friedel Crafts acylation which involves the acylation of 1,3-benzodioxole using propionyl chloride as the acylating agent in the presence of zinc oxide nanoparticles as a catalyst. This reaction results in the formation of a propionylated product. The reaction is facilitated by the Lewis acid catalysis provided by zinc oxide nanoparticles.arrow_forward(17, 18, 5) Give the relative rates of reaction of the four carboxylic acid derivatives below with aqueous sodium hydroxide to give the sodium carboxylate salt.arrow_forward
- For the following reaction scheme, identify by drawing the reagents b and d and the intermediate c that are formed in the synthesis of benzoic acid.arrow_forward1- Arrange the following compounds in order of decreasing reactivity towards hydrolysis. 2- Arrange the following chemical species in order of decreasing basicity.arrow_forwardDescribe the trends in the acidityand physical properties of carboxylicacids, and explain how their acidityvaries with their substituents.arrow_forward
- 1) How will you describe whether any compound has been oxidized or reduced? Support the answer with suitable examples. 2)Why carboxylic acid with a carbonyl group at 3rd position can be decarboxylated? 3) Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position? 4) List the following esters in order of decreasing reactivities towards hydrolysis with reason: Methyl benzoate, p-cyano methyl benzoate and p-hydroxy methyl benzoate 5)LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?arrow_forward(a) Draw the structures of the following compounds :(i) 4-Chloropentan-2-one (ii) p-Nitropropiophenone(b) Give tests to distinguish between the following pairs of compounds :(i) Ethanal and Propanal (ii) Phenol and Benzoic acid(iii) Benzaldehyde and Acetophenonearrow_forwardWhether the ortho-carboxy substituent acts as an intramolecular general-base catalyst or as an intramolecular nucleophilic catalyst can be determined by carrying out the hydrolysis of aspirin with 18O-labeled water and determining whether 18O is incorporated into ortho-carboxy-substituted phenol. Explain the results that would be obtained with the two types of catalysis.arrow_forward
- Explain 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. During the development of the optimized procedure for the experiment, it was found out that compound 1b can also be produced from the same set of starting materials. Propose a detailed reaction mechanism for the formation of 1b. Explain your answer. What factor/s may drive the formation of 1b over 1a?arrow_forwardCompound A is an alcohol that undergoes oxidation to produce compound B.Compound B is a ketone that gives positive triiodomethane reaction. Compound B isthen reacted with phenyl magnesium bromide, C6H5MgBr in the presence of aqueousacid to form compound C. Compound C has the molecular formula of C9H12O. Deducethe structure for compound A, B and C. PLEASE PROVIDE CLEAR DRAWINGS AND EXPLANATIONSarrow_forwardCompelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous−OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophllic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning