Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 15.SE, Problem 24AP
Look at the three resonance structures of naphthalene shewn in Section 15-6, and account for the fact that not all carbon—carbon bonds have the same length. The C1-C2 bond is 136 pm long, whereas the C2—C3 bond is 139 pm long.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
butene-1 acts on a combination of three reactants.Write the corresponding reactions.
a) H2, Br2, N2
b) Na, NaOH, HCl
c) H2O, HBr, KMnO4
d) Cl2, CO2, H2SO4
Acetonitrile (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 electronegativity
What is the saturation pressure of benzene at 700°C?
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...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 17-26 Account for the fact that acetone has a higher boiling point (56°C) than ethyl methyl ether (11°C) even though their molecular weights are almost the same.arrow_forward13-29 Show that if you add Steps 2a and 2b of the radical- chain mechanism for the autoxidation of a fatty acid hydrocarbon chain, you arrive at the following net equation: H I —CH2CH=CH—CH— + 0—0 • » Section of a fatty acid Oxygen hydrocarbon chain O—O—H I —CH2CH=CH—CH— A hydroperoxidearrow_forward17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C) have about the same molecular weight, yet their boiling points differ by almost 50°C. Explain this fact.arrow_forward
- In an advanced synthetic chemistry experiment, a researcher prepares a compound, ZY-7, by reacting a ketone (C5H10O) with hydroxylamine (NH2OH), followed by heating in the presence of an acid catalyst. The resulting compound, ZY-7, is then treated with a solution of sodium nitrite (NaNO2) and hydrochloric acid (HCl) at low temperature. Identify the class of compound that ZY-7 most likely belongs to after this series of reactions." A) Amide B) Oxime C) Nitro compound D) Diazonium salt E) Ester Don't use chatgpt please provide valuable answerarrow_forwardStarting with acetylene and ethylene oxide as the only sources of carbon atoms, show how to prepare the compound Q.)1,6-Hexanediolarrow_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_forward
- 12-47 Draw a structural formula for an alkene with the molecular formula C5H10that reacts with Br2to give each product. ch3 I (a) ch3c—chch3Br Br (c) CH2CHCH2CH2CH3Br Brarrow_forwardHydroboration-oxidation of 2-pentyne gives a mixture of two ketones, each with the molecular formula C5H10O. Propose structural formulas of these two ketones. Explain your proposal.arrow_forwardAzulene is a deep-blue hydrocarbon with resonance energy of 205 kJ>mol (49 kcal>mol). Azulene has ten pi electrons, so it might be considered as one large aromatic ring. Its electrostatic potential map shows one ring to be highly electron-rich (red) and the other to be electron-poor (blue). The dipole moment is unusually large (1.0 D) for a hydrocarbon. Show how this charge separation might arise.arrow_forward
- Consider the compounds 1-pentanol,CH3-CH2-CH2-CH2-CH2-OH, melting point -78C boiling point 138C, MW=88.15. 1,6-hexanediol ,HO-CH2-CH2-CH2-CH2-CH2-CH2-OH, mp 42C,bp=250C.MW=118.18. The compound 1,6-hexanediol is more soluble in water than 1-pentanol is. This is because 1,6-hexanediol.... 1) has more carbon atoms 2)has a higher molecular weight 3)has more -OH groups 4)is a solid at room temperaturearrow_forwardA compound with formula C6H14O gave the following HNMR:1.17 ppm, t, 3H1.20 ppm, s , 9H3.42 ppm, q, 2HDraw the structure of this compound.arrow_forwardAspirin, or 2-acetoxybenzoic acid, (C9H8O4) is often synthesised from salicylic acid.(i) Sketch and discuss any changes in the number of possible structural conformations ofaspirin relative to those of salicylic acid. (ii) Re-draw the structure predicted to be the lowest energy conformation of aspirin,indicating any expected stabilising and destabilising interactions. Justify your choice.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Acid-Base Titration | Acids, Bases & Alkalis | Chemistry | FuseSchool; Author: FuseSchool - Global Education;https://www.youtube.com/watch?v=yFqx6_Y6c2M;License: Standard YouTube License, CC-BY