11:40 TABLE 22.3 Additive parameters for predicting NMR chemical shifts of alkyl protons in CDCI₁₁ Base values Methyl 0.9 ppm Methylene 1.2 ppm Methine 1.5 ppm Group (Y) Alpha (a) substituent Beta (B) substituent Gamma (y) substituent H-C H-C-C-Y H- -R 0.0 0.0 0.0 -C=C 0.8 0.2 0.1 -C=C-Arb 0.9 0.1 0.0 -C=C(C=O)OR 1.0 0.3 0.1 -C=C-R 0.9 0.3 0.1 -C=C-Ar 1.2 0.4 0.2 -Ar 1.4 0.4 0.1 -(C=O)OH 1.1 0.3 0.1 -(C=O)OR 1.1 0.3 0.1 -(C=O)H 1.1 0.4 0.1 -(C=O)R 1.2 0.3 0.0 -(C=O)Ar 1.7 0.3 0.1 —(C=O)NH, 1.0 0.3 0.1 -(C=O)CI 1.8 0.4 0.1 -C=N 1.1 0.4 0.2 -Br 2.1 0.7 0.2 -Cl 2.2 0.5 0.2 -OH 2.3 0.3 0.1 -OR 2.1 0.3 0.1 -OAr 2.8 0.5 0.3 -O(C=O)R 2.8 0.5 0.1 -O(C=O)Ar 3.1 0.5 0.2 -NH₂ 1.5 0.2 0.1 -NH(C=O)R 2.1 0.3 0.1 —NH(C=O)Ar 2.3 0.4 0.1 TABLE 22.4 Additive parameters for predicting NMR chemical shifts of aromatic protons in CDCI 7.36 ppm³ Base value Group ortho meta para -CH3 -0.18 -0.11 -0.21 -CH(CH3)2 -0.14 -0.08 -0.20 -CH₂CI 0.02 -0.01 -0.04 -CH=CH₂ 0.04 -0.04 -0.12 -CH=CHAr 0.14 -0.02 -0.11 -CH=CHCO₂H 0.19 0.04 0.05 -CH=CH(C=O)Ar 0.28 0.06 0.05 (Continued) Group ortho meta para -Ar 0.23 0.07 -0.02 -(C=O)H 0.53 0.18 0.28 -(C=O)R 0.60 0.10 0.20 -(C=O)Ar 0.45 0.12 0.23 -(C=O)CH=CHAr 0.67 0.14 0.21 -(C=O)OCH 0.68 0.08 0.19 -(C=O)OCH2CH3 0.69 0.06 0.17 -(C=O)OH 0.77 0.11 0.25 -(C=O)CI 0.76 0.16 0.33 —(C=O)NH, 0.46 0.09 0.17 C=N 0.29 0.12 0.25 -F -0.32 -0.05 -0.25 -CI -0.02 -0.07 -0.13 -Br 0.13 -0.13 -0.08 -ОН -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -O(C=O)R -0.27 0.02 -0.13 -O(C=O)Ar -0.14 0.07 -0.09 ―NH₂ 0.71 การ -0.62 -N(CH.). -0.68 -0.15 -0.73 U.J 0.07 U.+1 -OAr -0.36 -0.04 -0.28 -0(C=0)R -0.27 0.02 -0.13 -O(C=O)Ar -0.14 0.07 -0.09 -NH₂ -0.71 -0.22 -0.62 -N(CH3)2 -0.68 -0.15 -0.73 -NH(C=O)R 0.14 -0.07 -0.27 NO₂ 0.87 0.20 0.35 TABLE 22.5 Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, 22.5 Table cis H C=C trans gem Base value 5.28 ppm cis gem trans Group 0.45 -0.22 -R -0.28 -CH=CH₂ 1.26 0.08 -0.01 -CH₂OH 0.64 -0.01 -0.02 -CH₂X (X=F, Cl, Br) 0.70 -0.11 -0.04 -(C=O)OH 0.97 1.41 0.71 -(C=O)OR 0.80 1.18 0.55 -(C=O)H 1.02 0.95 1.17 -(C=O)R 1.10 1.12 0.87 -(C=O)Ar 1.82 1.13 0.63 -Ar 1.38 0.36 -0.07 -Br 1.07 0.45 0.55 <-Cl -OR 1.08 0.18 0.13 1.22 -1.07 -1.21 -OAr 1.21 -0.60 -1.00 -0(C=O)R 2.11 -0.35 -0.64 —NH, NHR, -NR, 0.80 -1.26 1.21 -NH(C=O)R 2.08 -0.57 -0.72 a. There may be small QUESTION 5 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. GMU 2020 QUESTION 6 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020 QUESTION 7 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020