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ound 10 A Simplified IR Correlation Table ane CH CH: Alkenes (stretch) Aromatics (stretch) (stretch) (bend) (bend) Alkyne (stretch) Aldehyde (two peaks) Frequency fem", 3000-2850 1450 and 1375 1465 3100-3000 (out-of-plane bend) Alkene Aromatic Alkyne C-0* Aldehyde 3150-3000 Intensity 1000-700 Ketone Carboxylic Ester ca, 3300 2900-2 28 (acyer chemical shifts of aromatic protons in CDC, 7.36 pp Additive parameters for predicting NMR Table 22.4 Base value Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, pare eta ethe -0.21 -0.20 -0.04 -0.12 -0.11 0.05 Table 22.5 Grop -0.11 -0.08 -0.01 -0.04 -0.02 0.04 0.06 0.07 0.18 0.10 0.12 0.14 0.08 0.06 CH, -CHÍCH, CH,CI CHOH, -0.18 -0.14 0.02 0.04 0.14 0.19 H. trans gem CH7CHA -CH-CHCO,H CH-CHIC OIAr 0.05 -0.02 0.28 0.20 0.23 0.21 0.19 5.28 ppm 0.28 0.23 0.53 0.60 0.45 0.67 0.68 0.69 Base value ans gem -0.28 -0.01 -0.02 Grep 0.45 1.26 0.64 0.70 0.97 -0.22 0.06 -0.01 -0.11 -R 40IOR -CH-CH, -CH,OH -CHX (X=F, CI, Br) (COOH O-OIOR -O-OH -C-OIR -O-OA -0.04 0.71 0.55 10-07 C-OCH-CHAr O-OOCH, 0.17 1.41 0.25 0.33 0.17 0.25 -0.25 -0.13 -0.06 -0.43 -0.41 -0.28 -0.13 -0.09 0-OOCH,CH, 0.11 0.16 0.09 1.18 0.80 0.77 1.17 C-OOH C-OCI HC-OINH, -ON -f 0.95 1.12 0.76 0.46 1.02 0.87 0.63 1.10 0.12 -0.05 -0.07 -0.13 1.13 0.36 0.29 -0.32 -0.02 0.13 -0.53 -0.45 -0.36 1.82 -0.07 0.55 1.38 -Ar 0.45 1.07 1.08 0.13 0.18 -1.07 Br -1.21 -1.00 -0.64 Br -OH -OR -OAr -OC-OR -OC-OAr -0.14 122 1.21 2.11 0.80 -0.07 OR -OA -OC-OIR -NH, -NHR, -NR, -NHICOR -0.60 -0.35 -1.26 -0.57 -0.04 0.02 0.07 -0.22 -0.15 -0.07 0.20 1.21 -0.27 -0.14 -0.71 -0.68 -0.72 -0.62 -0.73 -0.27 0.35 2.08 re may be small differences in the chemical-shift values calculated from able and those measured from individual spectra. --NH, -NICH,), NHICOR -NO, 0.14 0.87 a. Base value is the measured chemical shift of benzene in CDCI, (1% solutic sye

ound 10 A Simplified IR Correlation Table ane CH CH: Alkenes (stretch) Aromatics (stretch) (stretch) (bend) (bend) Alkyne (stretch) Aldehyde (two peaks) Frequency fem", 3000-2850 1450 and 1375 1465 3100-3000 (out-of-plane bend) Alkene Aromatic Alkyne C-0* Aldehyde 3150-3000 Intensity 1000-700 Ketone Carboxylic Ester ca, 3300 2900-2 28 (acyer chemical shifts of aromatic protons in CDC, 7.36 pp Additive parameters for predicting NMR Table 22.4 Base value Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, pare eta ethe -0.21 -0.20 -0.04 -0.12 -0.11 0.05 Table 22.5 Grop -0.11 -0.08 -0.01 -0.04 -0.02 0.04 0.06 0.07 0.18 0.10 0.12 0.14 0.08 0.06 CH, -CHÍCH, CH,CI CHOH, -0.18 -0.14 0.02 0.04 0.14 0.19 H. trans gem CH7CHA -CH-CHCO,H CH-CHIC OIAr 0.05 -0.02 0.28 0.20 0.23 0.21 0.19 5.28 ppm 0.28 0.23 0.53 0.60 0.45 0.67 0.68 0.69 Base value ans gem -0.28 -0.01 -0.02 Grep 0.45 1.26 0.64 0.70 0.97 -0.22 0.06 -0.01 -0.11 -R 40IOR -CH-CH, -CH,OH -CHX (X=F, CI, Br) (COOH O-OIOR -O-OH -C-OIR -O-OA -0.04 0.71 0.55 10-07 C-OCH-CHAr O-OOCH, 0.17 1.41 0.25 0.33 0.17 0.25 -0.25 -0.13 -0.06 -0.43 -0.41 -0.28 -0.13 -0.09 0-OOCH,CH, 0.11 0.16 0.09 1.18 0.80 0.77 1.17 C-OOH C-OCI HC-OINH, -ON -f 0.95 1.12 0.76 0.46 1.02 0.87 0.63 1.10 0.12 -0.05 -0.07 -0.13 1.13 0.36 0.29 -0.32 -0.02 0.13 -0.53 -0.45 -0.36 1.82 -0.07 0.55 1.38 -Ar 0.45 1.07 1.08 0.13 0.18 -1.07 Br -1.21 -1.00 -0.64 Br -OH -OR -OAr -OC-OR -OC-OAr -0.14 122 1.21 2.11 0.80 -0.07 OR -OA -OC-OIR -NH, -NHR, -NR, -NHICOR -0.60 -0.35 -1.26 -0.57 -0.04 0.02 0.07 -0.22 -0.15 -0.07 0.20 1.21 -0.27 -0.14 -0.71 -0.68 -0.72 -0.62 -0.73 -0.27 0.35 2.08 re may be small differences in the chemical-shift values calculated from able and those measured from individual spectra. --NH, -NICH,), NHICOR -NO, 0.14 0.87 a. Base value is the measured chemical shift of benzene in CDCI, (1% solutic sye

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL3: Carbon (13c) Nmr Spectroscopy
Section: Chapter Questions
Problem 10E
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using the NMR spectrum tables, predict the shift for the carbon indicated by the arrows. 

ound 10 A Simplified IR Correlation Table ane CH CH: Alkenes (stretch) Aromatics (stretch) (stretch) (bend) (bend) Alkyne (stretch) Aldehyde (two peaks) Frequency fem", 3000-2850 1450 and 1375 1465 3100-3000 (out-of-plane bend) Alkene Aromatic Alkyne C-0* Aldehyde 3150-3000 Intensity 1000-700 Ketone Carboxylic Ester ca, 3300 2900-2 28 (acyer chemical shifts of aromatic protons in CDC, 7.36 pp Additive parameters for predicting NMR Table 22.4 Base value Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, pare eta ethe -0.21 -0.20 -0.04 -0.12 -0.11 0.05 Table 22.5 Grop -0.11 -0.08 -0.01 -0.04 -0.02 0.04 0.06 0.07 0.18 0.10 0.12 0.14 0.08 0.06 CH, -CHÍCH, CH,CI CHOH, -0.18 -0.14 0.02 0.04 0.14 0.19 H. trans gem CH7CHA -CH-CHCO,H CH-CHIC OIAr 0.05 -0.02 0.28 0.20 0.23 0.21 0.19 5.28 ppm 0.28 0.23 0.53 0.60 0.45 0.67 0.68 0.69 Base value ans gem -0.28 -0.01 -0.02 Grep 0.45 1.26 0.64 0.70 0.97 -0.22 0.06 -0.01 -0.11 -R 40IOR -CH-CH, -CH,OH -CHX (X=F, CI, Br) (COOH O-OIOR -O-OH -C-OIR -O-OA -0.04 0.71 0.55 10-07 C-OCH-CHAr O-OOCH, 0.17 1.41 0.25 0.33 0.17 0.25 -0.25 -0.13 -0.06 -0.43 -0.41 -0.28 -0.13 -0.09 0-OOCH,CH, 0.11 0.16 0.09 1.18 0.80 0.77 1.17 C-OOH C-OCI HC-OINH, -ON -f 0.95 1.12 0.76 0.46 1.02 0.87 0.63 1.10 0.12 -0.05 -0.07 -0.13 1.13 0.36 0.29 -0.32 -0.02 0.13 -0.53 -0.45 -0.36 1.82 -0.07 0.55 1.38 -Ar 0.45 1.07 1.08 0.13 0.18 -1.07 Br -1.21 -1.00 -0.64 Br -OH -OR -OAr -OC-OR -OC-OAr -0.14 122 1.21 2.11 0.80 -0.07 OR -OA -OC-OIR -NH, -NHR, -NR, -NHICOR -0.60 -0.35 -1.26 -0.57 -0.04 0.02 0.07 -0.22 -0.15 -0.07 0.20 1.21 -0.27 -0.14 -0.71 -0.68 -0.72 -0.62 -0.73 -0.27 0.35 2.08 re may be small differences in the chemical-shift values calculated from able and those measured from individual spectra. --NH, -NICH,), NHICOR -NO, 0.14 0.87 a. Base value is the measured chemical shift of benzene in CDCI, (1% solutic sye
Transcribed Image Text:ound 10 A Simplified IR Correlation Table ane CH CH: Alkenes (stretch) Aromatics (stretch) (stretch) (bend) (bend) Alkyne (stretch) Aldehyde (two peaks) Frequency fem", 3000-2850 1450 and 1375 1465 3100-3000 (out-of-plane bend) Alkene Aromatic Alkyne C-0* Aldehyde 3150-3000 Intensity 1000-700 Ketone Carboxylic Ester ca, 3300 2900-2 28 (acyer chemical shifts of aromatic protons in CDC, 7.36 pp Additive parameters for predicting NMR Table 22.4 Base value Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, pare eta ethe -0.21 -0.20 -0.04 -0.12 -0.11 0.05 Table 22.5 Grop -0.11 -0.08 -0.01 -0.04 -0.02 0.04 0.06 0.07 0.18 0.10 0.12 0.14 0.08 0.06 CH, -CHÍCH, CH,CI CHOH, -0.18 -0.14 0.02 0.04 0.14 0.19 H. trans gem CH7CHA -CH-CHCO,H CH-CHIC OIAr 0.05 -0.02 0.28 0.20 0.23 0.21 0.19 5.28 ppm 0.28 0.23 0.53 0.60 0.45 0.67 0.68 0.69 Base value ans gem -0.28 -0.01 -0.02 Grep 0.45 1.26 0.64 0.70 0.97 -0.22 0.06 -0.01 -0.11 -R 40IOR -CH-CH, -CH,OH -CHX (X=F, CI, Br) (COOH O-OIOR -O-OH -C-OIR -O-OA -0.04 0.71 0.55 10-07 C-OCH-CHAr O-OOCH, 0.17 1.41 0.25 0.33 0.17 0.25 -0.25 -0.13 -0.06 -0.43 -0.41 -0.28 -0.13 -0.09 0-OOCH,CH, 0.11 0.16 0.09 1.18 0.80 0.77 1.17 C-OOH C-OCI HC-OINH, -ON -f 0.95 1.12 0.76 0.46 1.02 0.87 0.63 1.10 0.12 -0.05 -0.07 -0.13 1.13 0.36 0.29 -0.32 -0.02 0.13 -0.53 -0.45 -0.36 1.82 -0.07 0.55 1.38 -Ar 0.45 1.07 1.08 0.13 0.18 -1.07 Br -1.21 -1.00 -0.64 Br -OH -OR -OAr -OC-OR -OC-OAr -0.14 122 1.21 2.11 0.80 -0.07 OR -OA -OC-OIR -NH, -NHR, -NR, -NHICOR -0.60 -0.35 -1.26 -0.57 -0.04 0.02 0.07 -0.22 -0.15 -0.07 0.20 1.21 -0.27 -0.14 -0.71 -0.68 -0.72 -0.62 -0.73 -0.27 0.35 2.08 re may be small differences in the chemical-shift values calculated from able and those measured from individual spectra. --NH, -NICH,), NHICOR -NO, 0.14 0.87 a. Base value is the measured chemical shift of benzene in CDCI, (1% solutic sye
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