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Solvolysis of 2-bromo-2-methylbutane in acetic acid containing sodium acetate gives three organic products. What are they?
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- pyridine reacts with 1-bromobutane to give?Electrophilic nitration of benzoic acid gives almost exclusively 3-nitrobenzoic acid. By drawing the appropriate resonance forms of the intermediate cations resulting from attack of [NO2]+, explain this result.Compelling 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 nucleophilic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.
- Compelling 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.How does the ratio of substitution product to elimination product formed from the reaction of propyl bromide with CH3O- in methanol change if the nucleophile is changed to CH3S-?Doxaprost, an orally active bronchodilator patterned after the natural prostaglandins , is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions involved in this synthesis. Q. Write equations to show that Step 6 can be brought about using either methanol or diazomethane (CH2N2) as a source of the -CH3 in the methyl ester.
- 2-methoxypyrrole is brominated exhaustively by treatment with Br2, while 2-methoxypyridine is selectively brominated at the 5-position. Explain thedifferences in reactivity, and the regioselectivity of the pyridine bromination,using resonance structures as part of your explanation.Identify the major products in the reaction of (R)-2-brimopentane with sodium cyanide in DMSOIdentify A, B, and C, intermediates in the synthesis of the ve-membered ring called an α-methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.