Concept explainers
Interpretation:
The structure of the compound having molecular formula
Concept introduction:
In
The number of signals in a spectrum gives information about the type of carbon atoms present in the structure of the compound.
In
The electronegative atom/group decreases the shielding of the carbon atom to which it is attached.
Index of hydrogen deficiency (IHD) is calculated by the equation as follows:
Here,
Oxygen atoms do not disturb the index of hydrogen deficiency.
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Chapter 16 Solutions
CAREY: ORGANIC CHEMISTRY
- Compound H (C8H6O3) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens solution. Following is its 1H-NMR spectrum. Deduce the structure of compound H.arrow_forwardPropose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardAn IR spectrum, a 13C NMR spectrum, and a 1H NMR spectrum were obtained for an unknown structure with a molecular formula of C8H18O. Draw the structure of this compound.arrow_forward
- Compound 2 has molecular formula C6H12. It shows three signals in the 1H-NMR spectrum, one at 0.96 ppm, one at 2.03 ppm, and one at 5.33 ppm. The relative integrals of these three signals are 3, 2, and 1, respectively. Provide structure for compound 2, explain how you reached your conclusion.arrow_forwardThe 1H-NMR spectrum of Compound C shows five signals – δ 2.38 (1H, dt), 2.72 (1H, dt), 5.34 (1H, t), 5.49 (2H, ddd), 6.27 (2H, dd) ppm. Its 13C-NMR spectrum has four signals – δ 26, 58, 127, 129 ppm. In the compound’s mass spectrum, the M+1 peak appears at m/z = 115. An M+2 peak, whose intensity is roughly one-third that of the M+1 peak, also appears. Suggest a structure for this compound.arrow_forwardidentify the compound with molecular formula C2H6O that gives this 1H NMR spectrum.arrow_forward
- An unknown compound, C4H10O gave the following proton NMR data: Singlet at 3.32 ppm (3H) Triplet at 0.94 ppm (3H) Triplet at 3.35 ppm (2H) Multiplet 1.47 ppm (2H) What is the structure of the compound?arrow_forwardCompound B has molecular formula C9H12. It shows five signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.22 ppm, a septet of integral 1 at 2.86 ppm, a singlet of integral 1 at 5.34 ppm, a doublet of integral 2 at 6.70 ppm, and a doublet of integral 2 at 7.03 ppm. The 13C-NMR spectrum of B shows six unique signals (23.9, 34.0, 115.7, 128.7, 148.9, and 157.4). Identify B and explain your reasoning.arrow_forwardAssume that you have a compound with the formula C4H8O. a) How many double bonds and/or rings does your compound contain? b) If your compound shows an infrared absorption peak at 1715 cm-1, what functional group does it have? c) If your compound shows a single 1H NMR absorption peak at 2.1 δ, what is its structure?arrow_forward
- An unknown compound has the molecular formula C9H10O and the Carbon-13 NMR spectrum shown below. Using this information, draw the structure of the unknown compoundarrow_forwardDraw the H1 NMR spectra of ethylcyclopropane. Draw the chemical structure and predict the proton splitting and chemical shifts.arrow_forwardCompound A exhibits two signals in its 'H NMR spectrum at 2.64 and 3.69 ppm and the ratio of the absorbing signals is 2:3. Compound B exhibits two signals in its 'H NMR spectrum at 2.09 and 4.27 ppm and the ratio of the absorbing signals is 3:2. Which compound corresponds to CH;O,CCH,CH2CO,CH3 (dimethyl succinate) and which compound corresponds to CH;CO,CH2CH,O,CCH; (ethylene diacetate)?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
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