Concept explainers
Interpretation:
The structure for a hydrocarbon with the following spectral characteristics is to be identified.
Mass spectrum: M+ at 120.
1HNMR spectrum: 7.25δ (5H, broad singlet); 2.90δ (1H, septet, J=7 Hz); 1.22δ (6H, doublet, J=7 Hz).
Concept introduction:
The molecular ion peak gives the approximate molecular mass of the compound. In 1HNMR spectrum
To identify:
The structure for a hydrocarbon with the following spectral characteristics.
Mass spectrum: M+ at 120. 1HNMR spectrum: 7.25δ (5H, broad singlet); 2.90δ (1H, septet, J=7 Hz); 1.22δ (6H, doublet, J=7 Hz).
Want to see the full answer?
Check out a sample textbook solutionChapter 15 Solutions
Organic Chemistry
- Compound 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_forwardPropose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardKetones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of the compound produced by reaction of 2-butanone with NaBH4 if it has an IR absorption at 3400 cm-1 and M+=74 in the mass spectrum?arrow_forward
- Propose structures for compounds that fit the following mass-spectral data: (a) A hydrocarbon with M+=132 (b) A hydrocarbon with M+=166 (c) A hydrocarbon with M+=84arrow_forwardThe mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.arrow_forwardAddition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows 1H-NMR resonances at 2.88 (3H), 3.00 (3H), 4.67 (2H), 7.93 (1H), 7.83 (1H), and 8.68 (1H). Assign a structure to the species giving this spectrum.arrow_forward
- Nitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?arrow_forwardWhen measured on a spectrometer operating at 200 MHz, chloroform (CHCl3) shows a single sharp absorption at 7.3 δ. (a) How many parts per million downfield from TMS does chloroform absorb? (b) How many hertz downfield from TMS would chloroform absorb if the measurement were carried out on a spectrometer operating at 360 MHz? (c) What would be the position of the chloroform absorption in δ units when measured on a 360 MHz spectrometer?arrow_forwardmolecular formula C5H11OCl find structure from the H1 nmr spectraarrow_forward
- The 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 for a compound of molecular formula C7H14O2 with an IR absorption at 1740 cm−1 and the following 1H NMR data: Absorption ppm Relative area singlet 1.2 9 triplet 1.3 3 quartet 4.1 2arrow_forwardThe mass spectrum of a compound with a molecular formula C9H10O is shown below. Which compound would you expect to give rise to the mass spectra shown below? A) Benzyl methyl ketone B) 3-Methyl-2,3-dihydro-benzofuran C) 2-Allylphenol D) Benzenepropanal E) 1-bromo-1-butenearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning