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- 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_forwardThe 1H and 13C NMR spectra of compound A, C8H9Br, are shown. Propose a structure for A, and assign peaks in the spectra to your structure.arrow_forwardThe mass spectrum and 13C NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.arrow_forward
- Acidcatalyzed dehydration of 3hydroxy3phenylcyclohexanone leads to an unsaturated ketone. What possible structures are there for the product? At what position in the ER spectrum would you expect each to absorb? If the actual product has an absorption at 1670 cm-1, what is its structure?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_forwardThe proton NMR spectrum for a compound with formula C10H12O2 is shown below. The infrared spectrum has a strong band at 1711 cm-1. The broadband-decoupled 13C NMR spectral results are tabulated along with the DEPT135 and DEPT90 information. Draw the structure of this compound.arrow_forward
- Ketones 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_forwardMass spectrometry of an unknown compound revealed a molecular ion at m/z 100.09. The IR spectrum, the ¹³C NMR spectrum, and the ¹H NMR spectrum are shown below. Draw the structure of this compound. 4000 220 3000 200 180 160 2000 M 1500 Wavenumbers (cm-¹) 140 120 100 1H 80 6H 1000 40 3H 20 ppm 500arrow_forwardC5H10O2 H Determine H and C Spectra for the compundarrow_forward
- Treatment of butan-2-one (CH3COCH2CH3) with strong base followed byCH3I forms a compound Q, which gives a molecular ion in its massspectrum at 86. The IR (> 1500 cm−1 only) and 1H NMR spectra of Q aregiven below. What is the structure of Q?arrow_forwardAn unknown compound D exhibits a strong absorption in its IR spectrumat 1692 cm−1. The mass spectrum of D shows a molecular ion at m/z =150 and a base peak at 121. The 1H NMR spectrum of D is shown below.What is the structure of D?arrow_forwardPredict the structure of the compound using the information below. Kindly show what information are obtained for each spectra which may help in predicting the structure. From IR Spectra: See the attached picture From Mass Spectra: M+ = 216 peaks at 29 (base peak) and 188 From Proton and Carbon NMR Spectra: See attached picture.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning