Interpretation:
The structure of the compound using given spectroscopic data is to be elucidated.
Concept introduction:
NMR data indicates the number and type of protons or carbons present in a compound based on the number of signals obtained in
Mass spectra of a compound indicate the molecular ion peak which gives the molecular mass of the compound.
Want to see the full answer?
Check out a sample textbook solutionChapter FRP Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
- Acid-catalyzed hydrolysis of HOCH2CH2C(CH3)2CN forms compound A (C6H10O2). A shows a strong peak in its IR spectrum at 1770 cm-1 and the following signals in its 1H NMR spectrum: 1.27 (singlet, 6 H), 2.12 (triplet, 2 H), and 4.26 (triplet, 2 H) ppm. Draw the structure for A and give a stepwise mechanism that accounts for its formation.arrow_forwardThe IR and 1H-NMR spectra of a compound with molecular formula C4H7ClO2 are shown below. Your objective is to propose a structure for this compound, explaining how you reach your decision.arrow_forwardThis compound, (C10H1002), shows strong, sharp absorption between 1700 and 1720 cm, and strong, broad absorption over the region 2500- 3000 cm. Given this information and the following NMR data, please draw the structure of the compound in the box below. H-NMR: 2.34 ppm, s(3H); 6.38 ppm, d(1H); 7.18 ppm, d(1H); 7.44 ppm, d(2H); 7.56 ppm, d(2H); 12.0, s(1H) 19C-NMR: 167.82; 143.82; 139.96; 131.45; 129.37; 127.83; 111.89; 21.13arrow_forward
- Determine the structure of a compound based on the data given below. IR: 3200-35oocm-1 Mass: 74 (M+), 59 (100%), 56, 45 1H NMR: d 4.0 (bs, 1H), 3.5 (ddq, 1H), 1.5 (ddq, 1H), 1.4 (ddq, 1H), 1.0 (d, 3H), 0.9 (d, 3H)arrow_forwardThe 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_forwardAn unknown compound has a molecular formula of C4H6O2. Its IR spectrum shows absorptions at 3095, 1762, 1254, and 1118 cm -1. It exhibits the following signals in its 1H NMR spectrum (ppm): 2.12 (singlet,3H), 4.55 (doublets of doublets, 1H), 4.85 (doublet of doublets, 1H), 7.25 (doublets of doublets, 1H); and the following signals in its 13C NMR spectrum (ppm): 20.8, 100.4, 141.2, 168.0. Draw the structure of the unknown compoundarrow_forward
- Propose a structural formula for compound A, C4H10O, consistent with the following 1H-NMR and IR spectra. Please assign all the appropriate peaks in the IR and NMR spectra and provide a short narrative describing what structural information each piece of data provided.arrow_forwardCompound X of the molecular formula C7H10 has the 13C NMR spectrum (5 signals) shown below. On treatment with excess H2/Pt (catalytic hydrogenation), X is converted to methylcyclohexane. Propose a structure for X and justify your reasoning by clearly labeling each carbon signal and write out the reaction. 200 180 160 140 120 100 80 60 40 20arrow_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_forward
- There are several isomeric alcohols and ethers of molecular formula C5H12O. Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers. Isomer A: δ = 0.92 (t, 7.8 Hz, 3 H), 1.20 (s, 6H), 1.49 (q, 7.8 Hz, 2H), 1.85 (s, 1H) ppm Isomer B: δ = 1.19 (s, 9 H), 3.21 (s, 3H) ppmarrow_forwardThe structure of an ester could either be A or B: CH3 O O CH3 T || -C-OCH3 CH3-C CH3-C-O-C-CH3 CH3 CH3 A B Its ¹H NMR spectrum consists of two peaks at 80.9 and 83.6 (relative areas 3:1). Which compound is it? Describe the spectrum that would be expected if it had been the other ester.arrow_forward3. Propose a structure for an organic compound with molecular formula C3H1404 given the following 'H NMR and IR spectra. Draw the structure only, no need to interpret the spectra. 1H NMR Spectrum IR Spectrum Triplet Singlet d (6H) 8 (4H) 8 (4H) 1740 cm1 Quartetarrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY