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 41AP
Propose structures for compounds that fit the following descriptions:
(a) C10H14
1H NMR: 7.18 5 δ (4 H, broad singlet); 2.70 δ (4 H, quartet, J = 7 Hz); 1.20 δ (6 H, triplet, J = 7 Hz)
IR: 745 cm-1
(b) C10H14
1H NMR: 7.0 δ (4 H, broad singlet); 2.85 δ (1 H, septet, J = 8 Hz); 2.28 δ (3 H, singlet); 1.20 δ (6 H, doublet, J = 8 Hz)
IR: 825 cm-1
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound.
Please show work.
Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound.
Propose a structure for a compound of molecular formula C3H8O with an IR absorption at 3600–3200 cm−1 and the following NMR spectrum:
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
- The 1H-NMR spectrum of Compound D of molecular formula C10H12O shows three singlets – δ 2.20 (6H, s), 4.86 (4H), 7.10 (2H) ppm. Its 13C-NMR spectrum has five signals – 20, 74, 127, 135, 146 ppm. Suggest a structure for this compound.arrow_forwardPropose a structure for the compound that fits the following description. C10H14 7.0 δ, (4H, broad singlet) 2.85 δ (1H, septet J = 8 Hz) 1.20 δ (6H, doublet J = 8 Hz) 2.28 δ (3H, singlet) IR: 825 cm-1 5(a) Degree of the unsaturation of this compound is= , 5(b) Two peaks at 2.85 δ and 1.20 δ indicate that the compound has .......... group = 4(c) A peak at 2.28 δ indicates that the compound has ............. group= 4(d) IR absorption indicates the compound is .........-disubstituted = 4(e) The name of the compound is =arrow_forwardPropose a structure of compound C (molecular formula C10H12O) consistent with the following data. C is partly responsible for the odor and flavor of raspberries. Compound C: IR absorption at 1717 cm-1arrow_forward
- Propose a structure for D (molecular formula C9H9ClO2) consistent withthe given spectroscopic data. 13C NMR signals at 30, 36, 128, 130, 133,139, and 179 ppmarrow_forwardIdentify the structure of compound C (molecular formula C₁1 H14NO₂), which has an IR absorption at 1699 cm-¹ and the ¹H NMR spectrum shown below. ¹H NMR of C 9 2 H 2 H 11 8 7 6 5 2 H 4 6 H 3 3 H 2 1arrow_forwardTreatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.arrow_forward
- An unknown compound has a molecular formula of C4H6O2. Its IR spectrum shows absorptions at 3095, 1762, 1254, and 1118 cm -1. It exhibits the following signals in its 1H NMR spectrum (ppm): 2.12 (singlet,3H), 4.55 (doublets of doublets, 1H), 4.85 (doublet of doublets, 1H), 7.25 (doublets of doublets, 1H); and the following signals in its 13C NMR spectrum (ppm): 20.8, 100.4, 141.2, 168.0. Draw the structure of the unknown compoundarrow_forwardPropose a structure for the compound that fits the following description. C10H14 7.18 δ, (4H, broad singlet) 2.70 δ (4H, quartet J = 7 Hz) 1.20 δ (6H. triplet J = 7 Hz) IR: 745 cm-1 7(a) IR absorption indicate the compound is .........-disubstituted = 7(b) The name of the compound is =arrow_forwardPropose the structure of the following alcohol? Molecular formula C5H12O The following peaks are found in proton NMR spectrum 0.91 δ (3H, triplet) 1.19 δ (6Η, singlet) 1.50 δ (2H, quartet) 2.0 δ (1H, singlet)arrow_forward
- Compound A, MW 72, shows an IR absorption at 1711 cm-1 and a 1H NMR spectrum with peaks at 2.4 8 (2 H, quartet), 2.1 8 (3H, singlet) and 1.1 8 (3 H, triplet). Propose a structure for A. Drawingarrow_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardThe 1H and 13C NMR spectra below belong to a compound with formula C6H10O2. Propose a structure for this compound.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY