Concept explainers
Treatment of compound E (molecular formula
Compound E signals at
Compound F signals at
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Organic Chemistry
- When compound A (C5H12O) is treated with HBr, it forms compound B (C5H11Br). The 1H NMR spectrum of compound A has a 1H singlet, a 3H doublet, a 6H doublet, and two 1H multiplets. The 1H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identify compounds A and B.arrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forwardPropose a structure for compound X (molecular formula C6H12O2), which gives a strong peak in its IR spectrum at 1740 cm−1. The 1H NMR spectrum of X shows only two singlets, including one at 3.5 ppm. The 13C NMR spectrum is given below. Propose a structure for X.arrow_forward
- Identify the structure of compound C (molecular formula C11H15NO2), which has an IR absorption at 1699 cm−1 and the 1H NMR spectrum shown below.arrow_forwardThymol (molecular formula C10H14O) is the major component of the oil of thyme. Thymol shows IR absorptions at 3500–3200, 3150–2850, 1621, and 1585 cm−1. The 1H NMR spectrum of thymol is given below. Propose a possible structure for thymol.arrow_forwardA solution of acetone [(CH3)2C = O] in ethanol (CH3CH2OH) in the presence of a trace of acid was allowed to stand for several days, and a new compound of molecular formula C7H16O2 was formed. The IR spectrum showed only one major peak in the functional group region around 3000 cm−1, and the 1H NMR spectrum is given here. What is the structure of the product?arrow_forward
- Compound X (molecular formula C10H12O) was treated with NH2NH2, −OH to yield compound Y (molecular formula C10H14). Based on the 1HNMR spectra of X and Y given below, what are the structures of X and Y?arrow_forwardAn unknown compound C (molecular formula C4H8O3) exhibits IRabsorptions at 3600−2500 and 1734 cm−1, as well as the following 1HNMR spectrum. What is the structure of C?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_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_forwardAn unknown compound A has the molecular formula C4H8O2. Based on the following 1H NMR spectrum, what is the structure of compound A?arrow_forwardAddition of mesitylene to the strongly acidic solvent HF / SbF5 at -45 °C gives a new species which shows a 1H-NMR resonance at δ 4.67 (2H). Draw the structure of this species.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning