6. A sweet-scented compound with the molecular formula C₁H₁2O2, was isolated from a synthetic perfume. Deduce the structure for the unknown compound by using the IR spectrum and the 'H and "C NMR spectra shown below. Explain. 100 mw My % Transmittance 4000 3000 11 10 9 8 200 2000 1500 Wavenumber/cm 1000 6 5 4 180 160 140 120 100 80 60 9 m 500 20

6. A sweet-scented compound with the molecular formula C₁H₁2O2, was isolated from a synthetic perfume. Deduce the structure for the unknown compound by using the IR spectrum and the 'H and "C NMR spectra shown below. Explain. 100 mw My % Transmittance 4000 3000 11 10 9 8 200 2000 1500 Wavenumber/cm 1000 6 5 4 180 160 140 120 100 80 60 9 m 500 20

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions

Section30.SE: Something Extra

Problem 12VC

See similar textbooks

Similar questions

Ascaridole is a natural product that has been used to treat intestinal worms. Explain why the two methyls on the isopropyl group in ascaridole appear in its 1H-NMR spectrum as four lines of equal intensity, with two sets of two each separated by 7 Hz.
How could 1H NMR spectroscopy be used to distinguish between attachedpair of compounds
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?
Phenacetin was a widely used pain-reliving and fever deducing drug until the1970’s when it was banned due to it link to renal diseases and cancers or the upper urinary tract.Given the structure of phenacetin which of the statement below are true? 1. The 1HNMR spectrum of phenacetin shows 5 signals corresponding to the differentprotons in the structure2. The 13CNMR spectrum of phenacetin shows 6 signals for the carbons on the benzene ring.3. The N-H proton of phenacetin will likely present as a broad peak in the spectrum.4. The DEPT 135 spectrum will show 8 peaks (6 up and 2 down).5. The aromatic signals of the protons are expected to both have chemical shifts larger thanthat of benzene due to the electron withdrawing nature of the substituents. A) 3 and 5 are true D) 1 and 4 are trueB) Only 3 is true E) 2 and 5 are trueC) 3 and 4 are true
An unkown compound, which is insoluable in water but soluble in 10% aqueous sodium bicarbonate, yielded the given 1H NMR spectrum. What is the compound?
Treatment of 2-butanone (CH3COCH2CH3) with strong base followed by CH3I forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (>1500 cm–1 only) and 1H NMR spectrum of Q are given below. What is the structure of Q?
Where would you expect to find the 1H NMR signal of (CH3)2Mg relative to the TMS signal?
The NMR spectra for compound 1 were acquired in a 7.5 mg / 0.6 mL solution ofCDCl3 . The 1H and 13C peaks are also listedbelow. Provide a full analysis of the NMR spectra for compound 1. correct assignment of NMR spectra of both 13C spectra. correct rationalisation of 13C spectrum1H NMR (400 MHz, CDCl3) δ 7.73 (d, J = 9.5 Hz, 1H), 7.56 (ddd, J = 8.5, 7.5, 1.6 Hz, 1H),7.51 (dd, J = 7.5, 1.6 Hz, 1H), 7.36 (d, J = 8.5 Hz, 1H), 7.30 (dd, J = 8.5, 7.5 Hz, 1H), 6.45(d, J = 9.5 Hz, 1H).13C NMR (101 MHz, CDCl3) δ 160.79, 154.09, 143.43, 131.85, 127.87, 124.44, 118.86,116.94, 116.74.Note: There are two carbon peaks in the 13C spectrum that are so close together that they are not differentiable at the resolution in this experiment. you should be able to assign these peaks to one of two carbon atoms in 1.
From the spectra, determine the structure of the molecule.Remember to ignore the triad in the 13 C NMR spectrum at 77 ppm thatcomes from the NMR solvent
Three steroids were sent for UV analysis and their spectra showed absorptions at 209 nm, 24 nm and 284 nm, respectively. Match each steroid below with its lmax in its UV-Visible spectrum and explain how you assigned the spectra.
Could you unambiguously distinguish between the reactant and product using C-NMR spectroscopy? Why or why not?
Draw the structure of C10H18O2 which is consistent with the 13C NMR data below. Thepeak appearing at 14 ppm is actually two very close peaks.