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88 Infrared Spectroscopy When a molecular formula is given, it is advisable to calculate an index of hydrogen deficiency (Section 1.4). The index often gives useful information about the functional group or groups that may be present in the molecule. *1. In each of the following parts, a molecular formula is given. Deduce the structure that is con- sistent with the infrared spectrum. There may be more than one possible answer. (a) C 3 H 3 Cl (b) C 10 H 14 (c) C 7 H 9 N (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBERS (CM (^1600 1400) –1) 1200 1000 800 600 400 2.5 3 4 5 6 MICRONS 7 8 9 10 11 12 13 14 15 16 19 25 C 7 H 9 N 100 90 80 70 60 50 40 30 20 10 0 %^ TRANSMITTANCE 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 WAVENUMBERS (CM–1) 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE C 10 H 14 (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBERS (CM (^1600 1400) –1 (^1200) ) 1000 800 600 400 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE^ C^3 H^3 Cl P R O B L E M S www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn (c) C(c) C 77 HH N www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 3 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 3200200 22880000 24002400 20002000 11 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 6 www.chem4all.vnwww.chem4all.vn MICRONSMICRONS 7 8 www.chem4all.vnwww.chem4all.vnwww.chem4all.vn CC 10101010 H 14141414 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn (^0000) WAVENUMBERS (CMWAVENUMBERS (CM (^16001600 14001400) –1–1 (^12001200) )) 10001000 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 1414 www.chem4all.vnwww.chem4all.vn 1515 www.chem4all.vnwww.chem4all.vn 1616 www.chem4all.vnwww.chem4all.vn 19 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn
Problems 89 (d) C 7 H 8 O (e) C 8 H 11 N (f) C 7 H 7 Cl 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 WAVENUMBERS (CM–1) 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE C 7 H 7 Cl (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBERS (CM (^1600 1400) –1) 1200 1000 800 600 400 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE C 8 H 11 N 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 WAVENUMBERS (CM–1) 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE C 7 H 8 O www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn (f) C(f) C 7 H 7 ClCl 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Problems 91 ( j) C 10 H 12 (two six-membered rings) (k) C 5 H 10 N 2 (l) C 4 H 8 O 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 400 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %% AB SO RB AN CE TR AN SM TI TA NC E C 4 H 8 O (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBERS (CM (^1600 1400) –1) 1200 1000 800 600 400 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE C 5 H 10 N 2 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 WAVENUMBERS (CM–1) 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS % TRAN SMITTANCE C 10 H 12 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn (l)(l) CC 4 H 8 OO www.chem4all.vnwww.chem4all.vnwww.chem4all.vn 2.52.5 2.62.6 2.72.7 2.82.8 2.92.9 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 1414 1515 1616 1717 1818 1919 2121 22 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 5050 www.chem4all.vn T T A www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 0000 24002400 20002000 11880000 16001600 14001400 12001200 10001000 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 8 www.chem4all.vnwww.chem4all.vn 99 www.chem4all.vnwww.chem4all.vn 1010 www.chem4all.vnwww.chem4all.vn 1111 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn C 55 H 101010101010101010 N 222 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 40004000 36003600 32003200 28002800 24002400 20002000 18001800 16001600 14001400 12001200 10001000 800800 600600 400400 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn
*92 Infrared Spectroscopy 2. Ants emit tiny amounts of chemicals called alarm pheromones to warn other ants (of the same species) of the presence of an enemy. Several of the components of the pheromone in one species have been identified, and two of their structures follow. Which compound has the infrared spectrum shown? *3. The main constituent of cinnamon oil has the formula C 9 H 8 O. From the following infrared spectrum, deduce the structure of this component. (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBERS (CM (^1600 1400) –1 (^1200) ) 1000 800 600 400 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE 1677 cm– (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBER (^1600 1400) S (CM–1 (^1200) ) 1000 800 600 400 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS % TRAN SMITTANCE 1720 cm – C O H Citral C O H Citronellal www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn The main constituent of cinnamon oil has the formula CThe main constituent of cinnamon oil has the formula C spectrum, deduce the structure of this component.spectrum, deduce the structure of this component. www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 4 www.chem4all.vn 5 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn (^40004000 36003600 32003200 28002800 24002400 20002000 18001800) WAVENUMBERWAVENUMBER 16001600 14001400 12001200 10001000 800800 600600 400400 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 1010 www.chem4all.vnwww.chem4all.vn 1111 www.chem4all.vnwww.chem4all.vn 1212 www.chem4all.vnwww.chem4all.vn 1313 www.chem4all.vn 1414 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 1720 cm1720 cm1720 cm1720 cm1720 cm1720 cm –1–1–1–
94 Infrared Spectroscopy
5. In each part, choose the structure that best fits the infrared spectrum shown. *(a) *(b) O O O O A B C D 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 WAVENUMBERS (CM–1) 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS % TRANSMITTANCE 1712 cm– CH 2 CH 2 C O CH 2 CH 3 O CH 2 CH 2 C CH 2 CH 3 O O C CH 2 CH CH CH 3 O CH CH C O CH 2 CH 3 O A B C D www.chem4all.vnwww.chem4all.vnwww.chem4all.vn (b)(b) www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 40004000 36003600 32003200 28002800 24002400 20002000 18001800 16001600 14001400 12001200 10001000 800800 600600 400400 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 6 www.chem4all.vnwww.chem4all.vn MICRONSMICRONS 77 8 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 1712 cm1712 cm CHCHCH CHCHCH CHCHCH 33
Problems 95 *(c) (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBERS (CM (^1600 1400) –1) 1200 1000 800 600 400 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE H N CH 2 CH 3 CH 3 N CH 3 CH 2 CH 3 NH 2 CH 2 CH 3 NH 2 A B C D (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBERS (CM (^1600 1400) –1) 1200 1000 800 600 400 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS %^ TRANSMITTANCE 178 0 cm– www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 40004000 33600600 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 4 www.chem4all.vnwww.chem4all.vn 5 www.chem4all.vn 2020 1010 00 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 3 www.chem4all.vnwww.chem4all.vnwww.chem4all.vn CHCH 2 NHNH 22 CHCH 33 AA BB C www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 80000 600600 400400 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn
Problems 97 (f) (g) 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE 1727 cm- CH 3 (CH 2 ) 7 H (^) C H H C C C O CH(CH 2 ) 6 C O O CH 3 (CH 2 ) 7 H C H H C C O CH 3 CH 3 H CH 2 CH (CH 2 ) 8 C H A C D B 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE 1675 cm- CH 3 CH 2 CH 3 CH 3 CH 3 CH (^3) CH 3 CH 3 CH 3 CH 2 O CH 3 O CH 3 O O A B C D www.chem4all.vnwww.chem4all.vnwww.chem4all.vn 2.5 2.6 2.72.7 2.82.8 2.92.9 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 9090 100 www.chem4all.vnwww.chem4all.vnwww.chem4all.vn 7 www.chem4all.vn C HH HH CC www.chem4all.vn OO www.chem4all.vn CHCH 33 (CH(CH 22 )) 7 www.chem4all.vn HH CCC CCC AA www.chem4all.vn 40004000 38003800 36003600 34003400 32003200 30003000 28002800 26002600 24002400 22002200 20002000 18001800 16001600 14001400 12001200 10001000 800800 600600 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 1414 1515 1616 1717 18 1918 19 WAVENUMBERSWAVENUMBERS www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn AA BB CC DD
9898 Infrared SpectroscopyInfrared Spectroscopy (h) (i) 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE NH 2 NH^ CH^3 CH 3 CH 3 A B C N 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE NICOLET 20S 1690 cm- H H C O H C C O O CH 3 (CH 2 ) 4 CH 3 (CH 2 ) 3 CH 3 C H C A C D B CH 3 CH 2 CH 2 H C O H C C CH 3 CH 2 CH (^2) CH 2 CH 3 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 2.6 2.72.7 2.82.8 2.92.9 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn NHNH www.chem4all.vnwww.chem4all.vn CHCH 33 AA www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 40004000 38003800 36003600 34003400 32003200 30003000 28002800 26002600 24002400 22002200 20002000 18001800 16001600 14001400 12001200 10001000 800800 600600 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 1414 1515 1616 1717 1818 1919 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn WAVENUMBERSWAVENUMBERS www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn -1- www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn O H www.chem4all.vn 3
100 Infrared Spectroscopy 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE NICOLET 20S 1743 cm-
7. Assign a structure to each of the spectra shown. Choose from among the following 5-carbon esters: 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE 1743 cm- O CH 3 CH 2 C O CH CH 2 O CH 3 CH 2 CH 2 O C CH 3 O CH 3 C O CH 2 CH CH 2 O CH 2 CH (^) C O CH 2 CH 3 (^4000 3600 3200 2800 2400 2000 1800) WAVENUMBERS (CM (^1600 1400) –1) 1200 1000 800 600 400 100 2.5^3 4 5 6 7 8 9 10 11 12 13 14 15 16 19 90 80 70 60 50 40 30 20 10 0 MICRONS % TRANSMITT ANCE
1640 cm www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 2.72.7 2.82.8 2.92.9 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 1414 1515 1616 1717 18 1918 19 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn Assign a structure to each of the spectra shown. Choose from among the following 5-carbonAssign a structure to each of the spectra shown. Choose from among the following 5-carbon www.chem4all.vnwww.chem4all.vnwww.chem4all.vn 3800 36003600 34003400 32003200 3000 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn OO CHCH 3 CHCH 22 O www.chem4all.vn CHCH 22 www.chem4all.vn CHCH 2 O CHCH 22 CHCH www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 600600 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn
Problems 101
8. Assign a structure to each of the following three spectra. The structures are shown here. 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE NICOLET 20S 1735 cm- CH 3 CH 2 CH 3 O O O O O O 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 450 WAVENUMBERS 90 100 2.5^ 2.6^ 2.7^ 2.8^ 2.9^3 3.5^4 4.5^5 5.5^6 7 8 9 10 11 12 13 14 15 16 17 18 19 .
0.60. 0.80.
22 80 70 60 50 40 30 20 10 0 NEAT MICRONS AB SO RB AN CE %T RA NS MI TT AN CE NICOLET 20SX FT-IR 1725 cm- 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE 1763 cm- www.chem4all.vnwww.chem4all.vnwww.chem4all.vn Assign a structure to each of the following three spectra. The structures are shown here.Assign a structure to each of the following three spectra. The structures are shown here. www.chem4all.vnwww.chem4all.vnwww.chem4all.vn 40004000 38003800 36003600 34003400 32003200 30003000 28002800 26002600 24002400 22002200 20002000 18001800 16001600 14001400 12001200 10001000 800800 600600 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 1414 1515 1616 1717 18 1918 19 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn MICRONSMICRONS www.chem4all.vnwww.chem4all.vn CHCH 22 www.chem4all.vn O www.chem4all.vnwww.chem4all.vnwww.chem4all.vn OO www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 800800 600600 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 2.52.5 2.62.6 2.72.7 2.82.8 2.92.9 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 100100 www.chem4all.vnwww.chem4all.vnwww.chem4all.vn
Problems 103
10. Assign a structure to each of the spectra shown. Choose from among the following 5-carbon alcohols: 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE C CH CH 2 OH CH 3 CH 2 CH 2 CH 2 CH 2 OH CH 2 CH 2 CH 2 OH CH 2 CH 2 OH CH 3 CH 3 CH 3 CH 2 CH CH 2 C 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE 1773 cm- www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 2.52.5 2.62.6 2.72.7 2.82.8 2.92.9 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 100100 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn Assign a structure to each of the spectra shown. Choose from among the following 5-carbonAssign a structure to each of the spectra shown. Choose from among the following 5-carbon 40004000 38003800 36003600 34003400 32003200 30003000 28002800 26002600 24002400 22002200 20002000 18001800 16001600 14001400 12001200 10001000 800800 600600 2.52.5 2.62.6 2.72.7 2.82.8 2.92.9 33 3.53.5 44 4.54.5 55 5.55.5 66 77 88 99 1010 1111 1212 1313 1414 1515 1616 1717 1818 1919 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn MICRONSMICRONS www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn CHCH 22 CHCH 2 OHOH CHCH 33 www.chem4all.vn CHCH 22 CHCH www.chem4all.vn C www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn 40004000 38003800 36003600 34003400 32003200 30003000 28002800 26002600 24002400 22002200 20002000 18001800 16001600 14001400 12001200 10001000 800800 www.chem4all.vnwww.chem4all.vnwww.chem4all.vnwww.chem4all.vn
104 Infrared Spectroscopy
11. Substitution of an amino group on the para position of acetophenone shifts the CJO frequency from about 1685 to 1652 cm−^1 , whereas a nitro group attached to the para position yields a CJO frequency of 1693 cm−^1. Explain the shift for each substituent from the 1685 cm−^1 base value for acetophenone. 4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 WAVENUMBERS MICRONS 0 10 20 30 40 50 60 70 80 90 100 %T RA NS MI TT AN CE Books and Compilations of Spectra Bellamy, L. J., The Infrared Spectra of Complex Molecules, 3rd ed., John Wiley, New York, 1975. Colthrup, N. B., L. H. Daly, and S. E. Wiberley, Introduction to Infrared and Raman Spectroscopy, 3rd ed., Academic Press, New York, 1990. Lin-Vien, D., N. B. Colthrup, W. G. Fateley, and J. G. Grasselli, The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, Academic Press, New York, 1991. Nakanishi, K., and P. H. Solomon, Infrared Absorption Spectroscopy, 2nd ed., Holden–Day, San Francisco, 1998. Pouchert, C. J., Aldrich Library of FT-IR Spectra, Aldrich Chemical Co., Milwaukee, WI, 1985 (1st ed.) and 1997 (2nd ed.). Pretsch, E., T. Clerc, J. Seibl, and W. Simon, Tables of Spectral Data for Structure Determination of Organic Compounds, 3rd ed., Springer-Verlag, Berlin, 1998, 1989. Translated from the German by K. Biemann. Sadtler Standard Spectra, Sadtler Research Laboratories Division, Bio-Rad Laboratories, Inc., 3316 Spring Garden Street, Philadelphia, PA 19104-2596. Numerous FT-IR search libraries are available for computers. Silverstein, R. M., F. X. Webster, and D. Kiemle, Spectrometric Identification of Organic Compounds, 7th ed., John Wiley, New York, 2005. Szymanski, H. A., Interpreted Infrared Spectra, Vols. 1–3, Plenum Press, New York, 1980. Computer Programs that Teach Spectroscopy Clough, F. W., “Introduction to Spectroscopy,” Version 2.0 for MS-DOS and Macintosh, Trinity Software, 74 Summit Road, Plymouth, NH 03264; www.trinitysoftware.com R E F E R E N C E S “IR Tutor,” John Wiley, 1 Wiley Drive, Somerset, NJ 08875-
Pavia, D. L., “Spectral Interpretation,” MS-DOS version, Trinity Software, 74 Summit Road, Plymouth, NH 03264; www.trinitysoftware.com Schatz, P. F., “Spectrabook I and II and Spectradeck I and II,” MS-DOS and Macintosh versions, Falcon Software, One Hollis Street, Wellesley, MA 02482; www. falcon- software.com Web sites http://www.dq.fct.unl.pt/qoa/jas/ir.html This site lists a number of resources for infrared spec- troscopy, including databases, tutorials, problems, and theory. http://www.aist.go.jp/RIODB/SDBS/menu-e.html Integrated Spectral DataBase System for Organic Compounds, National Institute of Materials and Chemical Research, Tsukuba, Ibaraki 305-8565, Japan. This database includes infrared, mass spectra, and NMR data (proton and carbon-13) for a number of compounds. http://webbook.nist.gov/chemistry/ The National Institute of Standards and Technology (NIST) has developed the WebBook. This site includes gas phase infrared spectra and mass spectral data for compounds. http://www.chem.ucla.edu/~webnmr/index.html UCLA Department of Chemistry and Biochemistry in connection with Cambridge University Isotope Laboratories maintains a website, WebSpecta, which pro- vides NMR and IR spectroscopy problems for students to interpret. They provide links to other sites with problems for students to solve. IntroductionIntroduction 3rd ed., Academic3rd ed., Academic Lin-Vien, D., N. B. Colthrup, W. G. Fateley, and J. G.Lin-Vien, D., N. B. Colthrup, W. G. Fateley, and J. G. TheThe HandbookHandbook ofof InfraredInfrared andand RamanRaman CharacteristicCharacteristic FrequenciesFrequencies ofof OrganicOrganic Molecules,Molecules, Nakanishi, K., and P. H. Solomon,Nakanishi, K., and P. H. Solomon, Infrared AbsorptionInfrared Absorption 2nd ed., Holden–Day, San Francisco, 1998.2nd ed., Holden–Day, San Francisco, 1998. Aldrich Library of FT-IR Spectra,Aldrich Library of FT-IR Spectra, Chemical Co., Milwaukee, WI, 1985 (1st ed.) and 1997Chemical Co., Milwaukee, WI, 1985 (1st ed.) and 1997 Pretsch, E., T. Clerc, J. Seibl, and W. Simon,Pretsch, E., T. Clerc, J. Seibl, and W. Simon, Tables of SpectralTables of Spectral Data for Structure Determination of Organic Compounds,Data for Structure Determination of Organic Compounds, 3rd ed., Springer-Verlag, Berlin, 1998, 1989. Translated3rd ed., Springer-Verlag, Berlin, 1998, 1989. Translated from the German by K. Biemann.from the German by K. Biemann. SadtlerSadtler StandardStandard Spectra,Spectra, SadtlerSadtler ResearchResearch LaboratoriesLaboratories Division, Bio-Rad Laboratories, Inc., 3316 Spring GardenDivision, Bio-Rad Laboratories, Inc., 3316 Spring Garden Street, Philadelphia, PA 19104-2596. Numerous FT-IRStreet, Philadelphia, PA 19104-2596. Numerous FT-IR search libraries are available for computers.search libraries are available for computers. Silverstein,Silverstein, R.R. M.,M., F.F. X.X. Webster,Webster, andand D.D. Kiemle,Kiemle, Spectrometric Identification of Organic Compounds,Spectrometric Identification of Organic Compounds, “IR Tutor,” John Wiley, 1 Wiley Drive, Somerset, NJ 08875-“IR Tutor,” John Wiley, 1 Wiley Drive, Somerset, NJ 08875- 1272.1272. Pavia, D. L., “Spectral Interpretation,” MS-DOS version,Pavia, D. L., “Spectral Interpretation,” MS-DOS version, Trinity Software, 74 Summit Road, Plymouth, NH 03264;Trinity Software, 74 Summit Road, Plymouth, NH 03264; www.trinitysoftware.comwww.trinitysoftware.com Schatz, P. F., “Spectrabook I and II and Spectradeck I and II,”Schatz, P. F., “Spectrabook I and II and Spectradeck I and II,” MS-DOSMS-DOS andand MacintoshMacintosh versions,versions, FalconFalcon Software,Software, www.chem4all.vn position of acetophenone shifts the Cposition of acetophenone shifts the CJJO frequencyO frequency , whereas a nitro group attached to the, whereas a nitro group attached to the parapar position yields aposition yields a . Explain the shift for each substituent from the 1685 cm. Explain the shift for each substituent from the 1685 cm www.chem4all.vnwww.chem4all.vnwww.chem4all.vn 40004000 38003800 36003600 34003400 32003200 30003000 28002800 26002600 24002400 22002200 20002000 18001800 16001600 14001400 12001200 10001000 800800 600600 www.chem4all.vn
