Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 15.SE, Problem 15VC
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
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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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- Define Protons on Benzene Rings ?arrow_forwardWhich of the following are consistent with the requirements for aromaticity?I. A system with delocalized p electrons in a ring.II. 4n p electrons in the ring.III. All the ring atoms must be carbons.IV. (4n + 2) p electrons in the ring. Give the answer why.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 isobutylene and HFarrow_forward
- Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 î disappears when D2O is added.arrow_forwardCompounds A and B have molecular formula C9H10O. Identify their structures from the 1H NMR and IR spectra given.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 fuming sulfuric acid.arrow_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_forwardTo be aromatic, a molecule must have 4n + 2 πs electrons and must have a planar, monocyclic system of conjugation. Cyclodecapentaene fulfills one of these criteria but not the other and has resisted all attempts at synthesis. Explain.arrow_forwardCompound B has molecular formula C9H10. The IR spectrum is shown below. The 1H-NMR spectrum shows a multiplet at 7.2 ppm integrating to 4H, a triplet at 2.9 ppm integrating to 4H, and a triplet at 2.1 ppm integrating to 2 H. Suggest a structure for B and explain your reasoningarrow_forward
- Compounds 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_forwardCompound 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_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
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