Concept explainers
(a)
Interpretation:
The structure of optically inactive compound A with the molecular formula
Concept introduction:
Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an
(b)
Interpretation:
The structure of isomer of compound A that has a different melting point and almost identical NMR spectra as that of A is to be stated.
Concept introduction:
Many nuclei and electrons have spin. Due to this, a spin magnetic moment arises. The energy of this magnetic moment depends on the orientation of the applied magnetic field. In NMR spectroscopy, every nucleus has a spin. There is an angular momentum related to the spin. The difference between its resonance frequency and that of the reference standard is known as the chemical shift of a nucleus. Tetramethylsilane (TMS) is taken as reference.
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Organic Chemistry
- Compound 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_forwardPropose a structural formula for the analgesic phenacetin, molecular formula C10H13NO2, based on its 1H-NMR spectrum.arrow_forwardWhen a compound with molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following1H NMR spectrum. Identify the compound.arrow_forward
- The 1H-NMR spectrum of compound B,C7H14O , consists of the following signals: δ 0.9 (t, 6H), 1.6 (sextet, 4H), and 2.4 (t, 4H). Draw the structural formula of compound B.arrow_forwardCompounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.arrow_forwardBased on the following 1H-NMR data, what is the possible structure of the alcohol C5H11OH?arrow_forward
- These are the 1H RMN and IR spectrums of an A compound with formula C10H13NO2. When A reacts with NaOH in water and heat, B compound is formed, with formula C10H11NO. What are the structures of A and B?arrow_forwardAn organic compound B with formula C6H14O has the following: IR Spectroscopy 2974 cm-1, 1080 cm-1 Mass Spectrometry 102 (M+), 87, 73 1H NMR Spectroscopy Eight signals at δ 1.10 (d, 3H), 1.13 (dd, 3H), 1.14 (dd, 3H), 1.59 (ddq, 1H), 1.60 (ddq, 1H), 3.19 (ddq, 1H), 3.51 (dq, 1H), 3.50 (dq, 1H). Compound B is obtained by the reaction of compound A with NaH followed by CH3CH2Br. The stereochemistry of A is "S" Using this information, deduce a plausible structure for Compound A with correct stereochemistry.arrow_forwardHow could 1H NMR spectroscopy be used to distinguish among isomers A, B, and C?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning