A carbonyl compound with an a hydrogen rapidly equilibrates with its corresponding enol. Give the structure for the enol tautomer(s) of the following compounds: (i). cyclopentanone (ii). ethyl acetate (iii). phenylacetone
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- In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Write the structure of each intermediate. Explain why a racemic product is formed.Compelling evidence for the existence of a tetrahedral intermediate innucleophilic acyl substitution was obtained in a series of elegantexperiments carried out by Myron Bender in 1951. The key experimentwas the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3)labeled at the carbonyl oxygen with 18O. Bender did not allow thehydrolysis to go to completion, and then examined the presence of alabel in the recovered starting material. He found that some of therecovered ethyl benzoate no longer contained a label at the carbonyloxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedralintermediate.
- tert-Butoxycarbonyl azide was developed as a reagent for peptide synthesis at OWL's home institution, the University of Massachusetts, by Prof. L.A. Carpino. It is prepared by treating tert-butoxycarbonyl chloride with sodium azide. Propose a structure for the initially-formed intermediate in this reaction.When 2-methylcyclohexanone is treated with pyrrolidine, two isomeric enamines areformed.Why is enamine A with the less substituted double bond the thermodynamicallyfavored product? (You will find it helpful to examine the models of these twoenamines.)Compound A is a derivative of the carbohydrate perosamine, which is found in the antibiotic perimycin. When A is treated with acetic anhydride in methanol, a monoacyl derivative B (C9H17NO5) is obtained in 73% yield. What is the structure of compound B?
- Give the major organic product of the following reaction sequences (d & e).Muscone synthesis is possible via an intramolecular Prins reaction. The starting point is cyclododecatriene, which his subjected topartial ozonolysis.With one aldehyde group protected,the other is reacted with isobutenyl magnesium chloride, and the protecting group is hydrolysed off. Then follows what is formally a Prins reaction,and etherification results in cyclisation to the bicyclic dihydropyran. Hydrogenation (at high T) finally gives racemic muscone. a. How to remove the protective group? b. What happens if you don't use a protective group?Muscone synthesis is possible via an intramolecular Prins reaction. The starting point is cyclododecatriene, which his subjected topartial ozonolysis.With one aldehyde group protected,the other is reacted with isobutenyl magnesium chloride, and the protecting group is hydrolysed off. Then follows what is formally a Prins reaction,and etherification results in cyclisation to the bicyclic dihydropyran. Hydrogenation (at high T) finally gives racemic muscone. a. What is the protective group used in the muscone synthesis above? b. What is the name of the reagent used as the protecting group? c. What groups are protected in the above muscone synthesis ?
- Acetoxybenzene (PhOC(=O)OCH3) is much less reactive than ethoxybenzene (PhOCH2CH3) in electrophilic aromatic substitution reactions. Suggest an explanation for this result, based on an analysis of the inductive and resonance electronic effects of the two substituents on the stability of theWheland intermediate for para substitution by an electrophile E+Interestingly, reduction of the complex shown above mostly gives thealcohol enantiomer shown below after workup. a. Draw the other minor diastereomeric alcohol product. b. Briefly explain the diastereoselectivity of the reduction – why is oneenantiomer heavily favored? Draw a structure or structures to support youranswer.Give the structures of the two substrates that arerequired to synthesize the following drug againstschizophrenia using the Knorr pyrrole synthesis.