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Deduce the structure of a compound with molecular formula C,H1002 that produces the following 'H NMR spectrum and 13C NMR spectrum: Proton NMR 10 Chemical Shift (ppm) Carbon NMR 128.8- 128.4 126.8 35.8 30.7 179.9 140.4 180 160 140 120 100 80 60 40 20

Deduce the structure of a compound with molecular formula C,H1002 that produces the following 'H NMR spectrum and 13C NMR spectrum: Proton NMR 10 Chemical Shift (ppm) Carbon NMR 128.8- 128.4 126.8 35.8 30.7 179.9 140.4 180 160 140 120 100 80 60 40 20

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Deduce the structure of C9H10O2 and determine the structure of an OH.
TABLE 16.2 CHEMICAL SHIFTS FOR PROTONS IN DIFFERENT ELECTRONIC ENVIRONMENTS TYPE OF PROTON CHEMICAL TYPE OF PROTON CHEMICAL SHIFT (6) SHIFT (6) Deduce the structure of a compound with molecular Alkyl halide Methyl R-CH3 0.9 2-4 formula C,H1002 that produces the following 'H NMR spectrum and 13C NMR spectrum: R-C-X Mathylene 1.2 Alcohol R-0-H 2-5 CH2 Proton NMR Methine 1.7 Vinylic 4.5-6.5 -CH Allylic -2 Aryl 6.5–8 Alkynyl R-=-H ~2.5 Aldehyde - 10 10 H. Chemical Shift (ppm) Aromatic ~2.5 Carboxylic acid 12 methyl -CH3 Carbon NMR 128.8- 128.4 TABLE 16.3 MULTIPLICITY INDICATES NUMBER OF NEIGHBORING PROTONS NUMBER OF NEIGHBORS MULTIPLICITY RELATIVE INTENSITIES 126.8 35.8- -30.7 140.4 – OF INDIVIDUAL PEAKS 179.9 1 Doublet 1:1 180 160 140 120 100 80 60 40 20 Triplet 1:2:1 Chemical Shift (ppm) 1:3:3:1 Quartet Quintet 1:4: 6:4:1 Sextet 1:5:10:10:5:1 Septet 1:6:15:20:15:6:1 Determine the structure of an alcohol with molecular formula CgH14O that exhibits the following DEPT-135 spectrum: -C=C- C-N C-o sp'-hybridized carbon atoms. p-hylridized carbon atoms (methyl, sp>-hybridized carbon methylene, and methine groups). Carbon atoms of p-hybridized carbon carbonyl groups. These carbon atoms are highly deshicldod. atoms as well as DEPT-135 atoms that are deshielded by electronegative atoms. 70 60 40 30 20 10 220 150 100 50 O ppm Chemical Shift (ppm) FIGURE 16.22 The general location of signals produced by different types of carbon atoms. TABLE 16.4 SIGNAL PATTERNS FOR DEPT 13c SPECTROSCOPY CH, CH2 CH BROADBAND DECOUPLED DEPT -90 | DEPT -135
Transcribed Image Text:TABLE 16.2 CHEMICAL SHIFTS FOR PROTONS IN DIFFERENT ELECTRONIC ENVIRONMENTS TYPE OF PROTON CHEMICAL TYPE OF PROTON CHEMICAL SHIFT (6) SHIFT (6) Deduce the structure of a compound with molecular Alkyl halide Methyl R-CH3 0.9 2-4 formula C,H1002 that produces the following 'H NMR spectrum and 13C NMR spectrum: R-C-X Mathylene 1.2 Alcohol R-0-H 2-5 CH2 Proton NMR Methine 1.7 Vinylic 4.5-6.5 -CH Allylic -2 Aryl 6.5–8 Alkynyl R-=-H ~2.5 Aldehyde - 10 10 H. Chemical Shift (ppm) Aromatic ~2.5 Carboxylic acid 12 methyl -CH3 Carbon NMR 128.8- 128.4 TABLE 16.3 MULTIPLICITY INDICATES NUMBER OF NEIGHBORING PROTONS NUMBER OF NEIGHBORS MULTIPLICITY RELATIVE INTENSITIES 126.8 35.8- -30.7 140.4 – OF INDIVIDUAL PEAKS 179.9 1 Doublet 1:1 180 160 140 120 100 80 60 40 20 Triplet 1:2:1 Chemical Shift (ppm) 1:3:3:1 Quartet Quintet 1:4: 6:4:1 Sextet 1:5:10:10:5:1 Septet 1:6:15:20:15:6:1 Determine the structure of an alcohol with molecular formula CgH14O that exhibits the following DEPT-135 spectrum: -C=C- C-N C-o sp'-hybridized carbon atoms. p-hylridized carbon atoms (methyl, sp>-hybridized carbon methylene, and methine groups). Carbon atoms of p-hybridized carbon carbonyl groups. These carbon atoms are highly deshicldod. atoms as well as DEPT-135 atoms that are deshielded by electronegative atoms. 70 60 40 30 20 10 220 150 100 50 O ppm Chemical Shift (ppm) FIGURE 16.22 The general location of signals produced by different types of carbon atoms. TABLE 16.4 SIGNAL PATTERNS FOR DEPT 13c SPECTROSCOPY CH, CH2 CH BROADBAND DECOUPLED DEPT -90 | DEPT -135
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