Lecture 13 Organic Chemistry 1
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1 EM 232 rganic hemistry I at hicago Lecture 13 rganic hemistry 1 Professor Duncan Wardrop February 23,
2 EM 232 rganic hemistry I at hicago Spectroscopy & Spectrometry hapter 13 2
3 EM 232 rganic hemistry I at hicago Introduction to Analytical Methods Sections:
4 Spectroscopy vs. Spectrometry Spectroscopy study of the interaction of electromagnetic radiation with matter; typically involves the absorption of electromagnetic radiation Spectrometry evaluation of molecular identity and/or properties that does not involve interaction with electromagnetic radiation at hicago EM 232, Spring 2010 Slide 4 4
5 Spectroscopic Methods Method Infrared Spectroscopy Ultraviolet-Visible (UV-vis) Spectroscopy Mass Spectrometry Nuclear Magnetic Resonance Spectroscopy Measurement/Application vibrational states: stretching and bending frequencies of covalent bonds that contain a dipole moment functional group determination electronic states: energy associated with promotion of an electron in a ground state to an exited state chromophore determination molecular weight: of parent molecule and fragments produced by bombardment with free electrons fragment and isotope determination nuclear spin states: energy associated with spin states of nuclei in the presence of a magnetic field determine structural groups and connectivity at hicago EM 232, Spring 2010 Slide 5 5
6 Absorption/Transmission Spectroscopy: Simplified Principles sample absorbs different frequencies of light corresponding to molecular vibrations (IR) or electronic transitions (UV-vis) detector determines what frequencies of light passed through (transmittance) and what frequencies of light were absorbed (absorbance) at hicago EM 232, Spring 2010 Slide 6 6
7 Electromagnetic Spectrum shorter wavelength (λ) higher frequency (ν) higher energy (E) longer wavelength (λ) lower frequency (ν) lower energy (E) Electromagnetic Radiation propagated at the speed of light (3 x10 8 m/s) has properties of particles and waves energy is directly proportional to frequency energy is indirectly proportional to wavelength E = hν c = νλ at hicago EM 232, Spring 2010 Slide 7 7
8 Quantized Energy States Types of States Energy Range (λ) Spectroscopic Method Increasing Energy nuclear spin rotational vibrational radiofrequency 1-10 m microwave cm infrared μm NMR Microwave IR electronic ultraviolet nm UV-vis at hicago EM 232, Spring 2010 Slide 8 8
9 EM 232 rganic hemistry I at hicago Infrared Spectroscopy Sections:
10 Principles of Infrared Spectroscopy IR: Measures the vibrational energy associated with stretching or bending bonds that contain a dipole moment (µ). Stretching δ + δ + δ + δ δ δ δ Bending δ δ δ + δ + δ + at hicago EM 232, Spring 2010 Slide 10 10
11 Stretching & Bending Vibrations at hicago EM 232, Spring 2010 Slide 11 11
12 Dipole Moment more electronegative atom covalent 2 electron bond dipole arrow less electronegative atom δ (partially negatively charged) δ (partially positively charged) In order to measure the stretching or bending frequency of a covalent bond, it must have a dipole moment (μ). at hicago EM 232, Spring 2010 Slide 12 12
13 ooke s Law: Bonds are Like Springs Vibrational Energy Depends both on bond strength (spring force constant) and the mass of atoms (objects) attached ~ ν = k f * (m1 + m2) (m1 * m2) ~ ν = vibrational frequency in wavenumbers (cm -1 ) k = constant (1/2πc) f = force constant; strength of bond (spring) Trends: bond strength = frequency mass = frequency m 1, m 2 = masses (not molecular weights) of attached atoms at hicago EM 232, Spring 2010 Slide 13 13
14 Spring Analogy smaller mass = higher frequency = higher energy stronger spring (bond) = higher frequency = higher energy at hicago EM 232, Spring 2010 Slide 14 14
15 Wavenumber (ῡ) and Infrared Scale ῡ (cm -1 ) = 1 λ (cm) higher wavenumber (ῡ) = higher frequency (υ) = lower wavelength (λ) = higher energy (E) lower wavenumber (ῡ) = lower frequency (υ) = longer wavelength (λ) = lower energy (E) N- - (sp)- (sp2)- (sp3)- 2 (2380) N N fingerprint region wavenumber (cm -1 ) wavenumber = reciprocal of the wavelength measured in centimeters (cm); directly proportional to frequency at hicago EM 232, Spring 2010 Slide 15 15
16 Infrared Spectrum % Transmission Transmittance: amount of light that passes through sample; not absorbed by molecular vibrations Frequency: typically measured in wavenumbers; higher wavenumber = higher frequency = higher energy vibration Bands: frequency of vibration absorbed by molecules; can be broad or narrow; number of bands does not equal number of bonds Wavenumbers at hicago EM 232, Spring Slide 16 16
17 haracteristic Stretches - Alkanes hexane = sp 3 - bond stretching motion; general absorb around cm = - rocking motion when atom is part of a methyl group (- 3 ); cm Wavenumbers = scissor motion of - 3 hydrogen atoms; cm cm -1 = fingerprint region for organic molecules; typically complex and unhelpful at hicago EM 232, Spring 2010 Slide 17 17
18 haracteristic Stretches - Alkenes hexene 5 5: notice sp 2 - (~3100 cm -1 ) at higher frequency than sp3 - (~2950 cm -1 ) more s-character = stronger bond = higher frequency 4: also, = bond at higher frequency than - bond; ~1600 cm Wavenumbers at hicago EM 232, Spring Slide 18 18
19 haracteristic Stretches - Alkynes hexyne 7: notice sp - (~3300 cm -1 ) at higher frequency than sp 2 - (~3100 cm -1 ), which was higher than sp 3 - (~2950 cm -1 ) 6: stretch is very weak because carbons have almost identical electronegativities = small dipole moment at hicago EM 232, Spring 2010 Slide 19 19
20 haracteristic Stretches - Alcohols prop-2-en-1-ol (allyl alcohol) 5 9: hydroxyl groups (-) exhibit strong broad bands; ~3300 cm broad peak is a result of hydrogen bonding; width depends on solution concentration lower concentration = less hydrogen bonding = more narrow - band Wavenumbers at hicago EM 232, Spring Slide 20 20
21 haracteristic Stretches - NItriles N 8 3-hydroxy-propionitrile : nitriles ~2200 cm -1 nitriles ( N) absorb a greater magnitude of energy than alkynes ( ) because they have a larger dipole moment larger dipole moment = more intense peak Wavenumbers size of the dipole does NT affect frequency of vibration at hicago EM 232, Spring 2010 Slide 21 21
22 Example: Ester, Amine, Benzene N amino-benzoic acid butyl ester 60 10: strong carbonyl (=) band ~1700 cm : amines; secondary amines (-N) give one band; primary amines (- N2) gives two bands 4: several alkene bands ~1600 cm -1 for benzene ring = double bonds Wavenumbers at hicago EM 232, Spring Slide 22 22
23 haracteristic Stretches - arboxylic Acids cyclohex-2-enecarboxylic acid 60 10: strong carbonyl (=) band ~1700 cm : hydroxyl band (-) can be less intense and sharper in carboxylic acids : weak alkene band (=) since small dipole moment Wavenumbers at hicago EM 232, Spring Slide 23 23
24 haracteristic Stretches - Aldehydes hept-2-enal : usually two bands for - of aldehydes; may overlap with sp 3 - bands Wavenumbers at hicago EM 232, Spring Slide 24 24
25 Self Test Questions Which molecule is represented by the IR below? cyclobutanol 2-butanone ethyl vinyl ether 2-methyl-2-propen-1-ol 2-methylpropanal a. b. c. d. e. A. a B. b.c D.d at hicago EM 232, Spring 2010 Slide 25 25
26 Self Test Questions Which molecule is represented by the IR below? cyclobutanol 2-butanone ethyl vinyl ether 2-methyl-2-propen-1-ol 2-methylpropanal a. b. c. d. A. a B. b.c D.d at hicago EM 232, Spring 2010 Slide 26 26
27 Self Test Questions Which molecule is represented by the IR below? cyclobutanol 2-butanone ethyl vinyl ether 2-methyl-2-propen-1-ol 2-methylpropanal a. b. c. d. e. A. a B. b.c D.d at hicago EM 232, Spring 2010 Slide 27 27
28 Self Test Questions Which molecule is represented by the IR below? cyclobutanol 2-butanone ethyl vinyl ether 2-methyl-2-propen-1-ol 2-methylpropanal a. b. c. d. e. A. a B. b.c D.d at hicago EM 232, Spring 2010 Slide 28 28
29 Self Test Questions Which molecule is represented by the IR below? cyclobutanol 2-butanone ethyl vinyl ether 2-methyl-2-propen-1-ol 2-methylpropanal a. b. c. d. e. A. a B. b.c D.d at hicago EM 232, Spring 2010 Slide 29 29
30 Self Test Questions Which molecule is represented by the IR below? cyclobutanol 2-butanone ethyl vinyl ether 2-methyl-2-propen-1-ol 2-methylpropanal a. b. c. d. e. A. a B. b.c D.d at hicago EM 232, Spring 2010 Slide 30 30
31 Example cyclobutanol 2-butanone ethyl vinyl ether 2-methyl-2-propen-1-ol 2-methylpropanal a. b. c. d. e. Greater s character = stronger, shorter bonds = higher frequency at hicago EM 232, Spring 2010 A. a B. b.c D.d Slide 31 31
32 EM 232 rganic hemistry I at hicago Ultraviolet-Visible Spectroscopy Section: This topic will be covered in hapter
33 EM 232 rganic hemistry I at hicago Next Lecture... hapter 13: Sections 13.23,13.24, Problem Set 1 has been posted Quiz This Week... hapter 5 & 6 33
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