Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 15.SE, Problem 35AP
Calicene, like azulene (Problem 15-17), has an unusually large dipole moment for a hydrocarbon. Explain, using resonance structures.
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Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Give IUPAC names for the following compounds:Ch. 15.1 - Prob. 3PCh. 15.2 - Pyridine is a flat, hexagonal molecule with bond...Ch. 15.3 - Prob. 5PCh. 15.4 - Draw the five resonance structures of the...Ch. 15.4 - Prob. 7PCh. 15.4 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Prob. 10P
Ch. 15.6 - Prob. 11PCh. 15.6 - How many electrons does each of the four nitrogen...Ch. 15.SE - Give IUPAC names for the following substances (red...Ch. 15.SE - All-cis cyclodecapentaene is a stable molecule...Ch. 15.SE - 1, 6-Methanonaphthalene has an interesting 1H NMR...Ch. 15.SE - Prob. 16VCCh. 15.SE - Azulene, an isomer of naphthalene, has a...Ch. 15.SE - Give IUPAC names for the following compounds:Ch. 15.SE - Draw structures corresponding to the following...Ch. 15.SE - Prob. 20APCh. 15.SE - Prob. 21APCh. 15.SE - Draw and name all possible aromatic compounds with...Ch. 15.SE - Propose structures for aromatic hydrocarbons that...Ch. 15.SE - Look at the three resonance structures of...Ch. 15.SE - Prob. 25APCh. 15.SE - Prob. 26APCh. 15.SE - Look at the five resonance structures for...Ch. 15.SE - Prob. 28APCh. 15.SE - 3-Chlorocyclopropene, on treatment with AgBF4,...Ch. 15.SE - Prob. 30APCh. 15.SE - Prob. 31APCh. 15.SE - Prob. 32APCh. 15.SE - Which would you expect to be most stable,...Ch. 15.SE - How might you convert 1, 3, 5, 7-cyclononatetraene...Ch. 15.SE - Calicene, like azulene (Problem 15-17), has an...Ch. 15.SE - Pentalene is a most elusive molecule that has been...Ch. 15.SE - Prob. 37APCh. 15.SE - Prob. 38APCh. 15.SE - Compound A, C8H10, yields three substitution...Ch. 15.SE - Prob. 40APCh. 15.SE - Propose structures for compounds that fit the...Ch. 15.SE - Prob. 42APCh. 15.SE - Prob. 43APCh. 15.SE - N-Phenylsydnone, so-named because it was first...Ch. 15.SE - Prob. 45APCh. 15.SE - Prob. 46APCh. 15.SE - Prob. 47APCh. 15.SE - Propose a structure for a molecule C14H12 that has...Ch. 15.SE - The proton NMR spectrum for a compound with...Ch. 15.SE - The proton NMR spectrum of a compound with formula...Ch. 15.SE - Aromatic substitution reactions occur by addition...Ch. 15.SE - Prob. 52APCh. 15.SE - Consider the aromatic anions below and their...Ch. 15.SE - After the reaction below, the chemical shift of Ha...Ch. 15.SE - Prob. 55APCh. 15.SE - Azo dyes are the major source of artificial color...
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- 1, 6-Methanonaphthalene has an interesting 1H NMR spectrum in which the eight hydrogens around the perimeter absorb at 6.9 to 7.3 δ, while the two CH2 protons absorb at -0.5 δ. Tell whether it is aromatic, and explain its NMR spectrum.arrow_forward6- In a 1H-NMR spectra on a scale of 0 – 10 ppm, Show the exact locations in ppm of 1-the saturated hydrocarbons, 2- the unsaturated hydrocarbons, 3- the halogenatedhydrocarbons and 4- the aromatic hydrocarbons.arrow_forwardFirst Writedown which reaction it is? SN1, SN2, E1? Write a stepwise mechanism for the following reactions showing ALL intermediates. Use curved arrows to symbolize the flow of electrons to show how each of the intermediates and product are formed. Show all necessary lone pairs and formal charges.arrow_forward
- Starting with acetylene and 1-bromobutane as the only sources of carbon atoms, show how to synthesize the following. Q.) Decanearrow_forwardBenzoic acid, Ph-COOH (C6H5CO2H), is not soluble in water while it dissolves in ether (diethyl ether), (CH3CH2)2O. Yet upon treatment with sodium hydroxide, benzoic acid turns hydrophilic and dissolves in water. Provide chemical explanation of this observation.arrow_forwardElectrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with cyclohexanol and BF3arrow_forward
- Please explain why if the 13C & 1H NMR spectrum data below is the possible structure of known compound ' 1-(4'-methyl-[1,1'-biphenyl]-4-yl)ethanone'? (Suzuki Cross-Coupling) 1H NMR: 2.41 ppm, 3H, singlet, aromatic -CH3 2.64 ppm, 3H, singlet, ketone, -CH3 7.27-7.29 ppm, 2H,doublet, aromatic -CH 7.53-7.54 ppm, 2H,doublet, aromatic -CH 7.67-7.68 ppm, 2H,doublet, aromatic -CH 8.01-8.03 ppm, 2H,doublet, aromatic -CH 13C NMR 22 ppm, -CH3 attached to the aromatic ring 26 ppm, -CH3 attached to the ketone carbonyl 127 ppm, aromatic -CH 129 ppm, aromatic -CH 130.5 ppm, aromatic -CH 135 ppm, aromatic -CH 137 ppm, aromatic -CH 145 ppm, aromatic -CH 197 ppm, carbonyl carbon of ketone IR: A band at 3040 cm-1 is a stretching frequency of the C-H bond of the alkene. A band at 1672 cm-1 is a stretching frequency of the -C=O bond of ketone (alpha beta unsaturated ketone). A band at 1598 cm-1 is a stretching frequency of the C=C bond of the aromatic ring. A band at 1391 and 1362 cm-1 is a bending…arrow_forwardAcetonitrile (CH3CN) has resonance at 1.97 ppm, whereas methyl chloride (CH3Cl) has resonance at 3.05 ppm, even though the dipole moment of acetonitrile is 3.92 D and that of methyl chloride is only 1.85 D. The larger dipole moment for the cyano group suggests that the electronegativity of this group is greater than that of the chlorine atom. Explain why the methyl hydrogens on acetonitrile are actually more shielded than those in methyl chloride, in contrast with the results expected on the basis of electronegativityarrow_forwardRank the carboxylic acid derivatives 11-15 in order from most reactive to least reactive in an acyl substitution reaction and give a brief explanation of why they are ranked in this orderarrow_forward
- Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict the major products of the reactions of naphthalene with HNO3, H2SO4.arrow_forwardDraw the four resonance structures formed during bromination of methoxybenzene, CH3OC6H5, with Br2/FeBr3 to give para-bromomethoxybenzene and then circle the most stable resonance form.arrow_forwardPlease help with the following... Draw the bond line structured for the reactants and the products obtained in the following reactions: 1. m-tertbutyl benzoic acid + 3-methyl-1butene, HF 2. 3-chloro-2,6-dinitrotulene + sodium ethoxide, ethanol 3. o-methylanisole + isobutanol, BF3arrow_forward
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