DGD2_NZ

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Nov 24, 2024

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1 uOttawa.ca CHM3122: Applications of Spectroscopy DGD2, September 19 5:30 pm Presented by: Niayesh Zarifi
2 nzarifi@uottawa.ca Assignment 2 Question 22 Which isomer of nonanone is this?
3 nzarifi@uottawa.ca Assignment 3 Question 1 Which of the following compounds (a–d) is represented in each of the mass spectra that follow?
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4 nzarifi@uottawa.ca Assignment 3 Question 1 Which of the following compounds (a–d) is represented in each of the mass spectra that follow?
5 nzarifi@uottawa.ca Assignment 3 Question 1 Which of the following compounds (a–d) is represented in each of the mass spectra that follow?
6 nzarifi@uottawa.ca Assignment 3 Question 1 Which of the following compounds (a–d) is represented in each of the mass spectra that follow?
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7 nzarifi@uottawa.ca Assignment 3 Question 5 2-Methylpentanal and 4-methyl-2-pentanone each show a molecular ion peak in their respective mass spectra of m/z 100. The spectrum of one isomer shows fragment peaks at m/z 85, 58, 57 and 43. The other isomer gives fragment peaks at 71, 58, 57, 43 and 29. Which spectrum fits which compound?
8 nzarifi@uottawa.ca Assignment 3 Question 7 6. The EI spectrum of 3-hexanol is given below Rationalize the small size of the molecular ion peak. Assign structures to the species at m/z 85, 59 and 73 and rationalize their formation
9 nzarifi@uottawa.ca Infrared (IR) Spectroscopy Functional group identification Contains a LOT of information (Look for easy stuff) IR is not generally used to determine the whole structure of an unknown molecule. We don’t need to analyze every single peak
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10 nzarifi@uottawa.ca Interpreting IR spectra 1) Ignore the fingerprint region (<1200 cm -1 ) for this course
11 nzarifi@uottawa.ca Interpreting IR spectra 2) Look for sp/sp 2 (>3000 cm -1 ) and sp 3 (3000-2850 cm -1 ) C—H bonds
12 nzarifi@uottawa.ca Interpreting IR spectra 3) Look for acidic protons (>3200 cm -1 , broad)
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13 nzarifi@uottawa.ca Interpreting IR spectra 4) Look for C=O (~1860-1600 cm -1 , very strong signal)
14 nzarifi@uottawa.ca Interpreting IR spectra 5) Look for aldehyde C—H (2800-2700 cm -1 , medium to weak)
15 nzarifi@uottawa.ca Medium/ weak bands that might be useful
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16 nzarifi@uottawa.ca Trends (mainly for C=O) Increased wavenumber – Shorter C—O bond (stronger bond) – Inductive effects (EWG) – Increase in s character (ring strain) Decreased wavenumber Decrease in double bond character Delocalization through resonance
17 nzarifi@uottawa.ca Bottom line IR spectra contain a lot of information It can be overwhelming Don’t try to solve every peak (unless you’re explicitly asked to) Use IR as an additional resource for the other data you have!
18 nzarifi@uottawa.ca Assignment 4 Question 3 Identify the key absorbances in the IR spectra of the following molecules and identify the functional group(s) that produce them.
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19 nzarifi@uottawa.ca Assignment 4 Question 4 Propose a plausible structure for the following formula and IR spectrum
20 nzarifi@uottawa.ca Assignment 4 Question 10
21 nzarifi@uottawa.ca Trends (mainly for C=O) Increased wavenumber – Shorter C—O bond (stronger bond) – Inductive effects (EWG) – Increase in s character (ring strain) Decreased wavenumber Decrease in double bond character Delocalization through resonance
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22 nzarifi@uottawa.ca Assignment 4 Question 17 Suggest a reasonable structure for an unknown compound whose mass spectrum and infrared spectrum are shown here. Provide a mechanism or explanation to account for the indicated peaks.
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