(a) Using reactions studied in this chapter, show steps by which this
(b) Could the homologous products obtained in these two cases be relied upon to show infrared absorption in the
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Organic Chemistry
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Chemistry & Chemical Reactivity
- This problem is adapted from an experiment designed for undergraduate organic chemistry laboratories. (a) Reaction of (E)-1-(p-methoxyphenyl)propene with m-chloroperoxybenzoic acid converted the alkene to its corresponding epoxide. Give the structure, including stereochemistry, of this epoxide.(b) Assign the signals in the 1H NMR spectrum of the epoxide to the appropriate hydrogens. δ 1.4 (doublet, 3H) δ 3.8 (singlet, 3H) δ 3.0 (quartet of doublets, 1H) δ 6.9 (doublet, 2H) δ 3.5 (doublet, 1H) δ 7.2 (doublet, 2H) (c) Three signals appear in the range δ 55–60 in the 13C NMR spectrum of the epoxide. To which carbons of the epoxide do these signals correspond? (d) The epoxide is isolated only when the reaction is carried out under conditions (added Na2CO3) that ensure that the reaction mixture does not become acidic. Unless this precaution is taken, the isolated product has the molecular formula C17H17O4Cl. Suggest a reasonable structure for this product and write a reasonable mechanism…arrow_forwardThe treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formulaC5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.arrow_forward(2E,4Z,6Z,8E)-decatetraene has been cyclized to give 7,8-dimethy-1,3,5-cyclooctatriene. Predict the manner of ring-closure conrotatory or disrotatory for both thermal and photochemical reactions, and predict the stereochemistry of product in each case. Show how to get the answerarrow_forward
- Compound A, C5H10O, is one of the basic building blocks of nature. All steroids ans many other naturally occurring compounds are built from compound A. Spectroscopic analysis of A yields the following information. a) how many double bonds and/or rings does A have? b) From the IR spectrum, what is the identity of the oxygen-conataining functional group? c) what kinds of protons are responsible for the NMR absorptions listed d) propose a structure for Aarrow_forwardReaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2N≡C, along with the nitrile CH3CH2N≡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.arrow_forwardCompounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.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_forwardBirch reduction of 2-methoxynaphthalene gave a mixture of two isomeric compounds, each having the molecular formula C11H14O. Suggest reasonable structures for these compounds.arrow_forwardCompound A has molecular formula C4H10, and gives two monochlorides, B and C, on photochemical chlorination. Treatment of either of these monochlorides with potassium tert-butoxide gives the same alkene (C4H8) as the product, but B leads to just one isomer of the alkene, D, where C gives D and another isomer of the alkene, E. Treatment of monochlorides B and C with aqueous ethanol gives products F and G, respectively, both of which are of molecular formula C4H10O. What are the names of compounds A-G?arrow_forward
- Compound A whose molecular formula is C9H11ClO, is found to be aromatic, and on vigorous oxidation with hot, concentrated, basic potassium permanganate followed by acidification, a new aromatic, compound B with the molecular formula of C7H5ClO2 is formed. On treatment with bromine and a ferric bromide catalyst, compound B produces ONLY 2 monobrominated derivatives, compounds C and D, each having the molecular formula C7H4BrClO2. On treatment with sodium metal, compound A produces bubbles of hydrogen gas. Controlled oxidation of compound A with PCC first gives compound E, with formula C9H9ClO. Compound E produces a silver mirror with Tollen’s reagent. Mild oxidation of compound E by chromic acid produces compound F, with the molecular formula C9H9ClO2 which turns blue litmus red. When compound A is heated with concentrated sulfuric acid, a single compound G, whose molecular formula is C9H9Cl, is produced. On ozonolysis followed by reaction with dimethyl sulfide, compound G gives…arrow_forwardProvide the products of the reaction of 1-propene with HBr in the presence and absence of peroxide. Explain the mechanism of the formation of the products in detailarrow_forwardC9H10O2: IR absorption at 1718 cm–1. Propose a structure with data given.arrow_forward