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When toluene is sulfonated (concentrated
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- The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.arrow_forwardThe following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated with D2O in the presence of an acid catalyst, only two of the three -hydrogens exchange with deuterium. The -hydrogen at the bridgehead does not exchange. How do you account for the fact that two -hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of -hydrogens occurs.arrow_forwardA certain hydrocarbon, C7H10, yields the two products shown below upon oxidative cleavage with KMnO4/H3O+ . Deduce the structure of the hydrocarbon.arrow_forward
- 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. Assuming that the two side chains on the cyclopentanone ring are trans, how many stereoisomers are possible from this synthetic sequence?arrow_forwardIn the acid-catalyzed dehydration of 2-methyl-1-propanol, what carbocation would be formed if a hydride shift accompanied cleavage of the carbon–oxygen bond in the alkyloxonium ion? What ion would be formed as a result of a methyl shift? Which pathway do you think will predominate, a hydride shift or a methyl shift?arrow_forwardPlease be clear in your writing, solve step by step Compound A (C9H12), when hydrogenated by catalysis on Pd / C, absorbs 3 equivalents of H2 to give compound B (C9H18). Ozonolysis of compound A gives cyclohexanone (C6H10O). Compound A reacting with NaNH2 / NH3 followed by addition of CH3Br gave compound C (C10H14). What are the structures of compounds A, B, and C?arrow_forward
- Provide the necessary sequence of reactions to generate the products below from their respective starting materials.arrow_forwardDraw the structures of the intermediate bromonium and cyclic carbocation and propose mechanisms for all three steps.arrow_forwardComplete the following mechanism for the acid-catalyzed rearrangement of 1-vinyl-2-phenylcyclopropane to give both isomers (E / Z) of 5-bromo-5-phenyl-2-pentene employing the curved-arrow/arrow-pushing formalism.arrow_forward
- Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.)2,4,6-Trinitrotoluene (TNT)arrow_forwardState the characteristic of the SN2 and SN1 mechanism towards alkyl halide compounds based onmolecularity, reaction rate constant, formation of product(s), reactivity of alkyl halides and thestrength of nucleophile.arrow_forwardBenzene, C6H6 undergoes substitution reaction with concentrated nitricacid, HNO3 to produce compound L. The reaction of compound L withbromine, Br2 in the presence of iron tribromide, FeBr3 produced compoundM. Benzene also undergoes Fridel-crafts alkylation reaction withchloroethane, CH3CH2Cl using catalyst N to produce compound P (i) Draw the structural formula of L, M and P (ii) State catalyst N. (iii) Show the formation of electrophile that will be reacted with benzene for theformation of compound P.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning