Interpretation:
The name of the isomers that are separately formed under kinetically and thermodynamically control reactions of sulfonation of naphthalene is to be determined. The reason for the stability of one isomer over other is to be explained.
Concept Introduction:
On the basis of
On the basis of
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ORGANIC CHEMISTRY VOL 2
- Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. By what type of reaction is (B) converted to (C)?arrow_forwardE2 elimination takes place under the same conditions as SN2 substitution and the reactions compete with each other. Which of the following statements is true? a) E2 elimination and SN2 substitution proceed through the same intermediate step b) E2 elimination is only possible for compounds that react with the SN2 mechanism c) In competition, a strong base favors a substitution reaction d) Steric hindrance favors E2 eliminationarrow_forwardAn acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting pointsand somewhat different solubilities. Draw the structure of these twoproducts. Assign R and S to any stereogenic centers in the products.How are the two products related? Choose from enantiomers,diastereomers, constitutional isomers, or not isomers of each other.arrow_forward
- Compound C undergoes a chemical reaction with a reagent, resulting in the formation of two new compounds. Four potential stereoisomers of the product are shown below. e) Name the type of reaction and provide a possible reagent. f) Clearly assign all the stereocentres found in compound D, E, F and G using Cahn-Ingold-Prelog rules. g) Define the relationship between compound D, E, F and G. h) Identify the two stereoisomers which are likely to be formed from compound C.arrow_forwardRank the pKa values of acetic acid, ethanol, phenol, and explain the reason in detailarrow_forwardIdentify A, B, and C, intermediates in the synthesis of the five-membered ring called an α-methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.arrow_forward
- This is a transesterification reaction. It mechanistically is the same as a Fischer Esterification. Write a mechanism for the reaction. Include all lone pairs and formal charges present throughout the mechanism.arrow_forwardBiphenyl has the following structure.(a) Is biphenyl a (fused) polynuclear aromatic hydrocarbon?(b) How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?(c) The heat of hydrogenation for biphenyl is about 418 kJ>mol (100 kcal>mol). Calculate theresonance energy of biphenyl.(d) Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain thedifference in the resonance energies of naphthalene and biphenyl.arrow_forwardUse the four compounds shown below to answer the following questions: a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?b. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids?c. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?arrow_forward
- Use the four compounds shown below to answer the following questions: a. Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid? b. Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids? c. Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?arrow_forwardWhy are 2-nitrobenzoic acid and 2-chlorobenzoic acid stronger acids than benzoic acid? Aromatic Side-Chain Oxidation: o-Chlorobenzoic Acid from o-Chlorotoluenearrow_forwardThe bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown. (a) Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole. (b) Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline. (c) Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning