Concept explainers
Identify the structures of isomers A and B (molecular formula
Compound A: IR peak at
Compound B: IR peak at
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Organic Chemistry
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Chemistry: Structure and Properties
- 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_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_forwardCompound X (molecular formula C10H120) was treated with NH2NH2, ¯OH to yield compound Y (molecular formula C10H14). Match the 1H NMR spectra of X and Y to the corresponding structures of X and Y. Compound NH2NH2 Compound 'H NMR of X 6 H OH Y 1 H 5H 8. 6. 4 ppm or H NMR of Y 6 H 2H 5H 1 H multiplet multiplet 8. 6. 4. 3. 1 nnm 2. 2. 3, O:arrow_forward
- 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 reasoningarrow_forwardIdentify this compound with molecular formula C9H10O IR peak at 1742 cm-^1,H nmr data (ppm) at 2.15(singlet,3H),3.70(singlet.2H) and 7.20(broad singlet,5H)arrow_forwardDraw the structure of a compound, C4H8O3 that exhibits IR absorptions at 1710 and 2500-3000 cm-1 and thefollowing 1H NMR signals: 11.1 (1H, singlet), 4.14 (2H, singlet), 3.63 (2H, quartet), 1.26 (3H, triplet) ppm.arrow_forward
- The 1H-NMR spectrum of Compound D of molecular formula C10H12O shows three singlets – δ 2.20 (6H, s), 4.86 (4H), 7.10 (2H) ppm. Its 13C-NMR spectrum has five signals – 20, 74, 127, 135, 146 ppm. Suggest a structure for this compound.arrow_forwardIdentify the structures of isomers A (molecular formula C9H10O).Compound A: I R peak at 1742 cm−1; 1H NMR data (ppm) at 2.15 (singlet, 3H), 3.70 (singlet, 2 H), and 7.20 (broad singlet, 5 H).arrow_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_forward
- Identify the compound with molecular formula C8H10O that gives the IR and 1H NMR spectra shown here.arrow_forwardCompounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)arrow_forwardCompound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.25 ppm and two doublets, one at 7.28 ppm and one at 7.39 ppm. The singlet has an integral of three and the doublets each have an integral of two. The mass spectrum of A shows a peak at m/z = 126 and another peak at m/z = 128; the relative height of the two peaks is 3:1 respectively. - Identify what atom X is, explaining your reasoning - Identify Compound A, explaining your reasoningarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning