Concept explainers
(a)
Interpretation:
The strucutral formula for each of the given compound has to be proposed using the given NMR data.
Concept Introduction:
The
Chemical shift: The NMR spectrum of any compound is taken with reference to a standard compound called reference compound. Generally, tetramethylsilane (TMS) is taken as the reference compound. The methyl protons of TMS are equivalent and produces only one sharp peak at the rightmost end of the scale.
13C NMR Spectroscopy: This type of NMR splitting of signals tells us numbers of hydrogens atoms are attached to each carbon. The triangle rule (n+1) C. The chemical shift explains the different hybridization
(a)
Explanation of Solution
Index of Hydrogen Deficiency (IHD) calculation,
Given molecular formula F is
We calculate the
From the molecular formula
The one signal in the
There are also one
Therefore, the based on above spectral details the structure that is consistent with the all of these facts is 4-Bromo-1- ethyl ester.
(b)
Interpretation:
The strucutral formula for each of the given compound has to be proposed using the given NMR data.
Concept Introduction:
The
Chemical shift: The NMR spectrum of any compound is taken with reference to a standard compound called reference compound. Generally, tetramethylsilane (TMS) is taken as the reference compound. The methyl protons of TMS are equivalent and produces only one sharp peak at the rightmost end of the scale.
13C NMR Spectroscopy: This type of NMR splitting of signals tells us numbers of hydrogens atoms are attached to each carbon. The triangle rule (n+1) C. The chemical shift explains the different hybridization
(b)
Explanation of Solution
Index of Hydrogen Deficiency (IHD) calculation,
Given molecular formula F is
We calculate the
From the molecular formula
The one signal in the
There are also one
Therefore, the based on above spectral details the structure that is consistent with the all of these facts is 4-Bromo-1- methylacetamide.
(c)
Interpretation:
The strucutral formula for each of the given compound has to be proposed using the given NMR data.
Concept Introduction:
The
Chemical shift: The NMR spectrum of any compound is taken with reference to a standard compound called reference compound. Generally, tetramethylsilane (TMS) is taken as the reference compound. The methyl protons of TMS are equivalent and produces only one sharp peak at the rightmost end of the scale.
13C NMR Spectroscopy: This type of NMR splitting of signals tells us numbers of hydrogens atoms are attached to each carbon. The triangle rule (n+1) C. The chemical shift explains the different hybridization
(c)
Explanation of Solution
Index of Hydrogen Deficiency (IHD) calculation,
Given molecular formula F is
We calculate the
From the molecular formula
The one signal in the
There are also one
Therefore, the based on above spectral details the structure that is consistent with the all of these facts is acid substituted phenylacetamide.
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Chapter 21 Solutions
Organic Chemistry
- Compound A has molecular formula C5H8Br4 but shows only one singlet in the 1H-NMR spectrum. Suggest a structure for A and explain your reasoning.arrow_forwardWhen compound A (C5H12O) is treated with HBr, it forms compound B (C5H11Br). The 1H NMR spectrum of compound A has a 1H singlet, a 3Hdoublet, 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. Identifycompounds A and B.arrow_forward(a) Compound A has molecular formula C5H10O. It shows three signals in the 1H-NMR spectrum - a doublet of integral 6 at 1.1 ppm, a singlet of integral 3 at 2.14 ppm, and a quintet of integral 1 at 2.58 ppm. Suggest a structure for A and explain your reasoning. (b) Compound B has molecular formula C8H6O2. The IR, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for B and explain your reasoning. (c) Compound C has molecular formula C5H8O. The IR, mass, 1H-NMR, and 13C-NMR spectra are shown below, they are also downloadable for closer inspection by clicking the link under the spectral data. Suggest a structure for C and explain your reasoning.arrow_forward
- Compound C has molecular formula C5H8O. The IR, mass, 1H-NMR, and 13C-NMR spectra are shown below. Suggest a structure for C and explain your reasoning.arrow_forwardIdentify 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_forwardCompound B has molecular formula C9H10. The IR spectrum is shown below. The 1H-NMR spectrum shows a multiplet at 7.2 ppm integrating to 4H, a triplet at 2.9 ppm integrating to 4H, and a triplet at 2.1 ppm integrating to 2 H. Suggest a structure for B and explain your reasoningarrow_forward
- Identify the structure of compound C (molecular formula C11H15NO2),which has an IR absorption at 1699 cm−1 and the 1H NMR spectrumshown below.arrow_forwardTreatment of compound C (molecular formula C4H8O) with C6H5MgBr, followed by H2O, affords compound D (molecular formula C10H14O). Compound D has a strong peak in its IR spectrum at 3600–3200 cm−1. The 1H NMR spectral data of C and D are given. What are the structures of C and D? Compound C signals at 1.3 (singlet, 6 H) and 2.4 (singlet, 2 H) ppm Compound D signals at 1.2 (singlet, 6 H), 1.6 (singlet, 1 H), 2.7 (singlet, 2 H), and 7.2 (multiplet, 5 H) ppmarrow_forwardA and B are isomeric dicarbonyl compounds of the molecular formula C5H&O2. The 'H NMR spectrum of A contains a singlet at 2.05 ppm and another singlet at 5.40 ppm. The 'H NMR spectrum of B contains three signals: a singlet at 2.3 ppm, a triplet at 1.10 ppm and a quartet at 2.70 ppm. Suggest structures for A and B and draw them in their respective boxes below. 1st attemptarrow_forward
- 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_forwardCompound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardCompound C has the molecular formula C5H8O. The IR, 1H, 13C, and DEPT NMR spectra of this compound are shown below. (a) Calculate the double bond equivalent of compound C and briefly explain what the values obtains represents. Interpret the IR spectrum. (b) Based on the information provided, determine the structure of compound D.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning