Concept explainers
A compound with molecular formula
Trending nowThis is a popular solution!
Chapter 9 Solutions
ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
Additional Science Textbook Solutions
General Chemistry: Atoms First
Organic Chemistry (8th Edition)
General, Organic, and Biological Chemistry (3rd Edition)
Introductory Chemistry (5th Edition) (Standalone Book)
Organic Chemistry
Chemistry: An Introduction to General, Organic, and Biological Chemistry (13th Edition)
- Propose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardCompound A, a hydrocarbon with M+=96 in its mass spectrum, has the 13C spectral data given below. On reaction with BH3, followed by treatment with basic H2O2. A is converted into B, whose, 13C spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled l3C NMR: 26.8, 28.7, 35.7, 106.9, 149.7 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 Compound B Broadband-decoupled 13C NMR: 26.1, 26.9, 29.9, 40.5, 68.2 DEPT-90: 40.5 DEPT-135: positive peak at 40.5 ; negative peaks at 26.1, 26.9. 29.9, 68.2arrow_forwardThe mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. Kne appears af m/z=111 and the other appears at m/z=97. Identify the structure of each of these fragments.arrow_forward
- The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forwardThe mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. One appears at m/z = 111 and the other appears at m/z = 97. Determine the identity and structure of each of these fragmentsarrow_forwardIndicate two basic differences that exist between the spectra of 1H y 13C in NMR.arrow_forward
- Treatment of 2-methylpropanenitrile [(CH3)2CHCN] withCH3CH2CH2MgBr, followed by aqueous acid, affords compound V, whichhas molecular formula C7H14O. V has a strong absorption in its IRspectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91(triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and2.60 (septet, 1 H) ppm. What is the structure of V?arrow_forwardThe compound has a molecular formula of C5H10O and the following 13C spectrum. A proton NMR was measured, but the data was lost except for the fact that it showed three distinct signals: a singlet, a doublet, and a septet, all of which appear between 0 and 3 ppm. Identify the compound, and draw its 1H NMR.arrow_forwardPropose a structure given the 1H and 13C NMR spectra of the unknown compound. Assign chemical shifts to corresponding hydrogen and carbon atoms Molecular Formula: C5H10O3arrow_forward
- Propose a structure for a compound of molecular formula C,H1402 with an IR absorption at 1740 cm and the following 'H NMR data: Absorption ppm Relative Area singlet 1.2 9 triplet 1.3 3 quartet 4.1arrow_forwardThe infiared spectrum of a compound contains a strong absorption at 1702 cm-1. The mass spectrum of the compound is shown below. What is the structure of the compound? 100 10 50 70 m/z 80 100 110 120 Relative Intensityarrow_forwardAnalyze the 1H AND 13C NMR spectrum of C8H9NO given below and draw the structure of the compound.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning