Concept explainers
(a)
Interpretation:
The explaination for the observation that although biacetyl and
Concept introduction:
The dipole moment of a molecule is the measure of the polarity of the
(b)
Interpretation:
The explaination for the observation that
Concept introduction:
The UV-visible spectroscopy involves the excitation of the electrons in the molecule. In the
(c)
Interpretation:
The explanation for the observation that compound A has much weaker IR carbonyl absorption than compound B is to be stated.
Concept introduction:
Spectroscopy method is used to identify the structure of the molecule. It is based on the interactions between matter and
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Organic Chemistry
- Give the reagents and conditions necessary for the following conversion. A to B, B to D, B to C, B to E, E to F, E to G, G to H, H to I. Hence deduce the name and structural formula of the compounds C and I. Compare the procedure for converting F and E to G.arrow_forwardThis 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_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
- The reaction of 3,4-dimethyl-3-hexanol (3,4-dimethylhexan-3-ol) with HBr generates compound A as the major product. Treatment of compound A with a strong base gives two isomers of compound B as the major product, along with one isomer of compound C and one isomer of compound D as minor products, all of which have one double-bond equivalent. Identify compounds A, B, C, and D and give their names. By what mechanism does the reaction of 3,4-dimethyl-3-hexanol with HBr occur? By what mechanism does the reaction of A with strong base to form B occur? Propose reaction conditions for an alternative, one-step method for converting 3,4-dimethyl-3-hexanol directly to compound B.arrow_forwardγ-Butyrolactone (C4H6O2, GBL) is a biologically inactive compound that is converted to the biologically active recreational drug GHB (Section 19.5) by a lactonase enzyme in the body. Since γ-butyrolactone is more fat soluble than GHB, it is more readily absorbed by tissues and thus produces a faster onset of physiological symptoms. γ-Butyrolactone shows an absorption in its IR spectrum at 1770 cm−1 and the following 1H NMR spectral data: 2.28 (multiplet, 2 H), 2.48 (triplet, 2 H), and 4.35 (triplet, 2 H) ppm. What is the structure of γ-butyrolactone?arrow_forwardMolecules of 6,6-dinitrobiphenyl-2,2-dicarboxylic acid have no tetrahedral chiral center, and yet they can be resolved to a pair of enantiomers. Account for this chirality.arrow_forward
- Please propose a structural formula for compound A, C4H10O, consistent with the following 1H-NMR and IR spectra. Assign all the appropriate peaks in the IR and NMR spectra and provide a short narrative describing what structural information each piece of data provided.arrow_forwardThe sex attractant of the female arctiid moth contains, among other components, a compound of molecular formula C21H40 that yields on ozonolysis. What is the constitution of this material?arrow_forwardCompound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide (HC≡CNa) )with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), while hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O═CH(CH2)12CH═O on ozonolysis. Assign structures to compound A through E so as to be consistent with the observed transformations.arrow_forward
- 1. Compound A, C9H12, absorbs 3 equivalents of H2 on catalytic hydrogenation over palladium catalyst to give B, C9H18. On the treatment with acidic KMnO4, compound A gives among other things, a ketone that was identified as cyclohexanone. On reaction with NaNH2 in NH3, followed by addition of iodomethane, compound A gives a new hydrocarbon C, C10H14. What are the structures of A , B and C?arrow_forwardCompound A, C3H7Br, does not react with cold dilute potassium permanganate solution. Upon treatment with potassium hydroxide in ethanol, A gives only product B, C3H6. Unlike A, B decolourises potassium permanganate solution. Ozonolysis of Bgives C, C2H4O, and D, CH2O. Suggest the structural formulae of A, B, C and D.Write the equations for all the reactions involved.arrow_forwardCompound A(C10H12O)gives off oxygen on treatment with sodium metal and also decolorizes Br2 in CCl4 to give organic compound B. Compound A on treatment with I2 in NaOH gives iodoform and salt C which after acidification gives a white solid D(C7H6O2). Using knowledge of organic chemistry identify structures A,B,C and Darrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning