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How can this IR graph of the crude product be

How can this IR graph of the crude product be

Chemistry
Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question: How can this IR graph of the crude product be an evadience that proof it is pure and the same as the product in the reaction? 70 60 50 40 30 20 4000 3491.185 3500 3088285- 2935.7194 XXX OH 3000 Crude product IR graph TOM C + 3 2500 2000 Wavenumbers (cm-1) the MATIRA andia 9-anthracenemethanol N-methylmaleimide abned ba 1708247 H₂O A 1 hr 1405.200 -008 1991 1680.148- - 1295 203 1500 1063.038 977 200 808 no bol 1124.381- RR anom -009 998 13 789 109 728 016-722 52339- 581.374-832 560- 1000 500 OH 9-(hydroxymethyl)-13-methyl-9, 10- dihydro-9,10-[3,4]epipyrroloanthracene- 12,14-dione Product Use this example as a guide of how to write the answer (keep in mind that 9- anthracenmethanol is the starting material should compare with) label you're the IR graph The crude product was recrystallized from methanol to afford methyl 3- nitrobenzoate (0.246 g, 60 %) as white, needle-like crystals; IR: 3065, 1709, 1530, 1300, 690 (cm*¹). Comparison of the IR spectrum of the product (methyl 3-nitrobenzoate) with the IR spectrum of the starting material (methyl benzoate) revealed an absorption from N-O stretching in the product, which was not present in the starting material. This also confirmed successful nitration of the aromatic ring. The starting material, methyl benzoate contains a carbonyl substituent directly attached to the aromatic ring. Carbonyl substituents are electron withdrawing and decrease the reactivity of the arene ring, especially in the ortho and para positions. Carbonyls are meta-directors; therefore, nitration was expected to occur in the meta position. The IR of the final product had an absorption at 790 cm', which is indicative of meta-disubstituted arenes
Transcribed Image Text:Question: How can this IR graph of the crude product be an evadience that proof it is pure and the same as the product in the reaction? 70 60 50 40 30 20 4000 3491.185 3500 3088285- 2935.7194 XXX OH 3000 Crude product IR graph TOM C + 3 2500 2000 Wavenumbers (cm-1) the MATIRA andia 9-anthracenemethanol N-methylmaleimide abned ba 1708247 H₂O A 1 hr 1405.200 -008 1991 1680.148- - 1295 203 1500 1063.038 977 200 808 no bol 1124.381- RR anom -009 998 13 789 109 728 016-722 52339- 581.374-832 560- 1000 500 OH 9-(hydroxymethyl)-13-methyl-9, 10- dihydro-9,10-[3,4]epipyrroloanthracene- 12,14-dione Product Use this example as a guide of how to write the answer (keep in mind that 9- anthracenmethanol is the starting material should compare with) label you're the IR graph The crude product was recrystallized from methanol to afford methyl 3- nitrobenzoate (0.246 g, 60 %) as white, needle-like crystals; IR: 3065, 1709, 1530, 1300, 690 (cm*¹). Comparison of the IR spectrum of the product (methyl 3-nitrobenzoate) with the IR spectrum of the starting material (methyl benzoate) revealed an absorption from N-O stretching in the product, which was not present in the starting material. This also confirmed successful nitration of the aromatic ring. The starting material, methyl benzoate contains a carbonyl substituent directly attached to the aromatic ring. Carbonyl substituents are electron withdrawing and decrease the reactivity of the arene ring, especially in the ortho and para positions. Carbonyls are meta-directors; therefore, nitration was expected to occur in the meta position. The IR of the final product had an absorption at 790 cm', which is indicative of meta-disubstituted arenes
OIR table Nitrile Nitro C-N Carboxylic Acid C=0 O-H C-0 Aldehyde C=0 O=C-H Amide Ester C=0 N-H N-H Anhydride C=0 C=0 C-0 Ketone Acyclic Cyclic Table of Common IR Absorptions for Organic Functional Groups (1070-1150) 2210-2260 Arylketone stretch stretch stretch stretch stretch stretch stretch Detailed Description of Carbonyl Functional Group Absorptions stretch stretch bending stretch stretch stretch stretch stretch -Unsaturated stretch Stretch 1515-1560 1345-1385 1700-1725 2500-3300 1210-1320 1740-1720 2820-2850 2720-2750 1640-1690 3100-3500 1550-1640 1800-1830 & 1740- 1775 1735-1750 1000-1300 1750-1725 3-membered - 1850 4-membered-1780 5-membered-1745 6-membered-1715 7-membered - 1705 medium 1665-1685 1680-1700 strong, two bands strong strong, very broad strong strong medium, two bands strong (unsubstituted amides have two bands) strong, two bands strong two bands or more strong strong strong strong Functional Group Alcohol 0-H 0-H C-0 Alkane C-H -C-H Alkene C-H =C-H C=C Alkyl Halide C-F C-CI C-Br Alkyne T Amine C-H N-H (RNH₂) (R₂NH) C-N N-H Aromatic C-H C=C Ether Carbonyl C=0 C-O Table of Common IR Absorptions for Organic Functional Groups Type of Vibration stretch (H-bonded) stretch (free OH) stretch stretch bending stretch bending stretch stretch stretch stretch stretch stretch stretch stretch stretch bending stretch stretch Characteristic Absorptions (cm) stretch 3200-3600 3500-3700 1050-1150 2850-3000 1350-1480 3010-3100 675-1000 1620-1680 1000-1400 600-800 500-600 500 3300 2100-2260 3300-3500 1080-1360 1600 3000-3100 1400-1600 Intensity 1000-1300 strong, broad strong, sharp strong strong variable medium strong variable medium medium-weak, multiple b See Detailed Description of Carbonyl Functional Group Absorp (Conjugation shifts absorptions to lower wave numbers) 1670-1820 Stretch strong strong strong strong strong strong, sharp variable (not present in symmetrical a medium (1° amines have two ban (2 amines have one band, ofte medium, weak medium strong
Transcribed Image Text:OIR table Nitrile Nitro C-N Carboxylic Acid C=0 O-H C-0 Aldehyde C=0 O=C-H Amide Ester C=0 N-H N-H Anhydride C=0 C=0 C-0 Ketone Acyclic Cyclic Table of Common IR Absorptions for Organic Functional Groups (1070-1150) 2210-2260 Arylketone stretch stretch stretch stretch stretch stretch stretch Detailed Description of Carbonyl Functional Group Absorptions stretch stretch bending stretch stretch stretch stretch stretch -Unsaturated stretch Stretch 1515-1560 1345-1385 1700-1725 2500-3300 1210-1320 1740-1720 2820-2850 2720-2750 1640-1690 3100-3500 1550-1640 1800-1830 & 1740- 1775 1735-1750 1000-1300 1750-1725 3-membered - 1850 4-membered-1780 5-membered-1745 6-membered-1715 7-membered - 1705 medium 1665-1685 1680-1700 strong, two bands strong strong, very broad strong strong medium, two bands strong (unsubstituted amides have two bands) strong, two bands strong two bands or more strong strong strong strong Functional Group Alcohol 0-H 0-H C-0 Alkane C-H -C-H Alkene C-H =C-H C=C Alkyl Halide C-F C-CI C-Br Alkyne T Amine C-H N-H (RNH₂) (R₂NH) C-N N-H Aromatic C-H C=C Ether Carbonyl C=0 C-O Table of Common IR Absorptions for Organic Functional Groups Type of Vibration stretch (H-bonded) stretch (free OH) stretch stretch bending stretch bending stretch stretch stretch stretch stretch stretch stretch stretch stretch bending stretch stretch Characteristic Absorptions (cm) stretch 3200-3600 3500-3700 1050-1150 2850-3000 1350-1480 3010-3100 675-1000 1620-1680 1000-1400 600-800 500-600 500 3300 2100-2260 3300-3500 1080-1360 1600 3000-3100 1400-1600 Intensity 1000-1300 strong, broad strong, sharp strong strong variable medium strong variable medium medium-weak, multiple b See Detailed Description of Carbonyl Functional Group Absorp (Conjugation shifts absorptions to lower wave numbers) 1670-1820 Stretch strong strong strong strong strong strong, sharp variable (not present in symmetrical a medium (1° amines have two ban (2 amines have one band, ofte medium, weak medium strong
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