Interpretation:
The structure of phenacetin and phenetidine from the given data are to be determined.
Concept introduction:
Infrared spectroscopy is a simple, instrumental technique, which helps to determine the presence of various
It depends on the interactions of atoms or molecules with the
Infrared spectroscopy is most commonly used in the identification of the structure of the compound.
Infrared spectroscopy is the examination of the infrared light interacting with a molecule. The examination can be done in three ways, that is, by measuring absorption, emission, and reflection, and it can also measure the vibration of atoms.
Infrared absorption bands indicate the functional groups present in a compound. For example, carbonyl group shows a band from
Nuclear Magnetic Resonance (NMR) is one of the most capable analytical techniques used for determining the functional groups and how the atoms are structured and arranged in a molecule.
Few elements, such as
In
Induced magnetic field consists of electricity generated from movement in a magnetic field.
Any signal’s position on the X-axis in the
The number of signals in
The area covered by the signal is proportional to the number of equivalent protons causing the signal.
The hydrogen atom on adjacent carbon atoms splits the peak into two or more peaks. One, two, and three hydrogen atoms split the peak into two, three and four peaks, which further, is referred to as doublet, triplet or quartet.
The decrease in the electron density around a proton deshields the signal downfield at a larger value of chemical shift.
The increase in electron density shields the signal upfield at a lower value of chemical shift.
NMR data indicates the number and type of protons or carbons present in a compound based on a number of signals obtained in
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Organic Chemistry
- Phenacetin, a substance formerly used in over-the-counter headache remedies, has the formula C10H13NO2. Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, C8H11NO, whose 1H NMR spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, C6H7NO. What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?arrow_forwardCompound 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_forwardWhich of the following best differentiate the acetanilide from p-nitroacetanilide? p-nitroacetanilide will have 3 H-NMR peaks at around 7.26 ppm while acetanilide will only have 2. acetanilide will have have an N-H IR peak at 3200- 3400 while p-nitroactenilide won't. acetanilide will have 3 H-NMR peaks at around 7.26 ppm while p-nitroacetanilide will only have 2. p-nitroacetanilide will have have an N-H IR peak at 3200-3400 while actenilide won't.arrow_forward
- Using ChemDraw Predict 1H NMR spectra of acetophenone and the protonated acetophenone.arrow_forwardAnnotate the H-NMR spectra of Benzophenonearrow_forwardWhen acetophenone, hydroxelamine hydrochloride, and sodium hydroxide are reacted to synthesize acetophenone oxime, why is it necessary to add hydrochloric acid after the reaction to make it acidic?arrow_forward
- Each hydrogen of a primary amide typically has a separate 1H-NMR resonance, as illustrated by the separate signals for the two amide hydrogens of propanamide, which fall at δ 6.22 and δ 6.58. Furthermore, each methyl group of N,N-dimethylformamide has a separate resonance (δ 3.88 and δ 3.98). How do you account for these observations?arrow_forwardCompound H (C,H,O,) gives a precipitate when treated with hydroxylamine in aqueous ethanol and a silver mirror when treated with Tollens' solution. Following is its 'H-NMR spectrum. Deduce the structure of compound H. Compound H 2H IH IH IH 7 5 Chemical shift (8) 0 ppm 10 9. 8. 3. 2.arrow_forwardCompound A has molecular formula C8H8O. Its 1H-NMR spectrum shows a singlet of integral 3 at 2.58 ppm and a multiplet of integral 5 at 7.84 ppm. Its 13C-NMR shows six signals. The IR spectrum of A shows a noteworthy stretch at 1698 cm-1. - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows three singlets, one at 2.52 pm of integral 3, one at 6.67 ppm of integral 1, and one at 7.94 ppm of integral 2. The 13C-NMR spectrum of B shows six signals. - Identify compound B, explaining your reasoning Compound B is treated with methylmagnesium bromide and then aqueous acid to generate compound C. The 1H-NMR spectrum of C shows four singlets, one at 1.42 ppm of integral 6, one at 2.3 ppm of integral 1, one at 8.52 ppm of integral 2, and one at 8.97 ppm of integral 1. The 13C-NMR spectrum of C shows six signals. The IR spectrum of C shows a noteworthy broad stretch at 3326 cm-1. -…arrow_forward
- 17.36 Tamoxifen is an estrogen receptor modulator that is used in the treatment of breast cancer. Provide the missing reagents and the structure of compound A in the synthesis of tamoxifen. Page 707 HO (CH3)2N 1. C,H,MgBr 2. H + Compound A (CH3)2N Tamoxifenarrow_forwardCompound A has molecular formula C7H7X. Its ¹H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C- NMR shows five signals. The mass spectrum of A shows a peak at m/z 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoning Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The ¹H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively. - Identify compound B, explaining your reasoning Compound B is treated with sodium ethoxide to generate compound C. The ¹H-NMR spectrum of C shows…arrow_forwardhow to prepare phenylmethanamine from benzene ?arrow_forward
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