Organic Spectroscopy 1 Michaelmas Lecture 6 Dr Rob Paton.
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1 rganic Spectroscopy 1 Michaelmas 2011 Lecture 6 Dr Rob Paton robert.paton@chem.ox.ac.uk 1
2 Recap of Lecture 5 UV-vis Spectroscopy Measures the gaps between electronic energy levels Most useful for conjugated double bonds since the M-LUM energy gap is small enough to promote an electron in this spectral region Increasing conjugation leads to greater absorption, and a shift to absorption at longer wavelengths (λ max ) Characteristic absorption for certain classes of organic compounds may be predicted (albeit relatively crudely) using Woodward s rules Steric effects and geometric strain may prevent efficient conjugation, and therefore will affect UV-vis absorption wavelengths Infrared (IR) Spectroscopy Measures molecular vibrational energy levels Molecules vibrate in many ways simultaneously, however, fundamental normal modes give rise to characteristic IR absorptions. The strength of absorption depends on the change in dipole-moment of the vibrating group. 2
3 The X- region: cm -1 For example: C- bonds: 1-ethynyl-1-cyclohexene Typical C- stretching frequencies: sp 3 C- sp 2 C- sp C cm -1 usually C 3 and C 2 symmetric and antisymmetric stretches are seen cm -1 exact form depends on the number of alkene substituents cm -1 usually appears as a single sharp peak 3
4 Some C- stretches are diagnostically useful (Bohlmann bands): N- bonds: Slightly higher than C- stretches ( cm -1 ): N Me N N-methylaniline & aniline 4
5 - bonds: Very broad absorption around 3300 cm -1 is characteristic F 4-fluorophenol Carboxylic acids display a characteristic V-shape in the - absorption 1-cyclopentene-1-carboxylic acid 5
6 ydrogen bonding affects the strength of an - bond: pka: Steric factors inhibit -bonding: 2- t butyl-6-methylphenol 6
7 Example Problem Using NMR, UV-vis and IR: C 6 6 CCl 3 / - / 2 A + B (C ) A B λ max 285 (ε 16,000) λ max 255 (ε 10,000) δ 7.0 (d, 2), 7.8 (d, 2), 9.8 (s, 1), 10.4 (brs, 1)* δ (m, 4), 9.8 (s, 1), 10.9 (s, 1)* ν 3600 (dil. sol.) (conc. sol.), 1690 ν (no change on dilution.), 1660 *exchanges in D 2 7
8 The triple bond region: cm -1 C N and C C bonds: 1-Pentyne IR Spectrum propionitrile 8
9 ethylisocyanoacetate Cumulenes 3-methyl-1,2-butadiene (an allene) 9
10 The double bond region: cm -1 C=C bonds: Alkenes, aromatics oleyl alcohol E-4-nonene 10
11 methyl crotonate Nitro groups are also diagnostic: Nitrocyclohexane 11
12 Carbonyl Groups Learn these numbers! IR spectroscopy is particularly useful in identifying which of the several different kinds of carbonyl group is present in a molecule. C= double bonds show a strong absorption band since they have a large dipole moment. The position of the absorption is governed by the electronic structure. carbonyl group stretching frequency (approx.) increasing stretching frequency (stronger C= bond) R R' anhydrides R Cl acid chlorides R' R esters R aldehydes 1820 & 1760 cm cm cm cm -1 R Cl R Cl 1.18 Å 1.20 Å R R' ketones 1715 cm Å 12
13 R R' ketones 1715 cm Å decreasing stretching frequency (weaker C= bond) R acids R NR' 2 amides R SiR' 3 acylsilanes 1710 cm cm cm -1 R NR' 2 R NR' Å 1.25 Å carboxylates 1580 cm -1 R R Electron donating groups weaken the C= bond shifting IR frequency down Electron withdrawing groups strengthen the C= bond shifting the IR frequency up 13
14 Conjugation: Conjugated ketones Non-conjugated ketones C= stretch ca cm -1 C= stretch ca cm -1 Conjugation lowers the stretching frequency, typically by around 30 cm -1. Ring Strain: When a carbonyl is part of a ring, the C= stretching frequency depends on ring size: as ring size decreases, the carbonyl stretching frequency increases. X X X = C cm cm cm cm cm -1 X = 1727 cm cm cm cm -1 X = N cm cm cm cm cm cm cm -1 X X 14
15 Me N Me Me Me N pk a = -0.5 Stable to hydrolysis pk a = 5.3 ydrolyses in 2 / + in 45s CN Å C Å C= stretch 1650 cm -1 C= stretch 1732 cm -1 Kirby et al. Angewandte Chemie International Edition 1998, 37,
16 Example: Six derivatives of the steroid cholestane: match up the structures with the IR data A B C D E F Et Et Selected IR absorptions (s=strong, w=weak): Spectrum ν (cm -1 ) (s) 1724 (s), 1712 (s) 1730 (s), 1695 (s), 1642 (w) Spectrum ν (cm -1 ) (s), 1686 (s), 1608 (w) 1653 (s), (s), 1658 (w),
17 Example: The molecular mass of X has been determined by high-resolution mass spectrometry as What is the formula and structure of X? (masses : C: : ) IR spectrum of X 17
18 Example: It was envisaged that the condensation of two equivalents of ethyl acetoacetate with formaldehyde would produce agemanns ester. Is the product s IR spectrum consistent with this proposal? Et piperidine (cat.) then heat "agemann's ester" (2 equiv) C 2 Et Product IR spectrum 18
19 Example: Identify the product from the reaction of cyclohexenone and dimethylcopper lithium i) Me 2 CuLi C 7 12 ii) + Reactant IR spectrum Product IR spectrum 19
20 Example: Use the following IR and 1 NMR spectra to assign the structures of two isomers of C 6 12 verlay of X & Y IR spectra 1 NMR spectrum of X (ppm) 1 NMR spectrum of Y (ppm) 20
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