Quiz 5.1 – IR Spectroscopy 1. IR spectroscopy is most ...

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Ch. 5 – Spectroscopy

DAT Organic Chemistry Outline

Quiz 5.1 – IR Spectroscopy 1. IR spectroscopy is most useful for identifying: A. The stereochemistry of molecules B. A compound’s functional group C. Enantiomeric excess in a non-racemic mixture D. A compound’s purity 2. H2 doesn’t give an IR spectrum because: A. It isn’t possible to get an IR spectrum of a gas B. It has no atomic motions C. H2 doesn’t have a net dipole moment D. None of the above 3. The IR spectrum of an organic compound has no strong absorptions from 1600 to 2600 or any above 3000. What functional group is it likely to contain? A. Alcohol B. Aldehyde C. Amine D. ether 4. A strong infrared (IR) absorption band between 1750 and 1700 indicates which of the following functional groups?

5. Which of the following would give a strong IR absorption band at 1720 cm-1?

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Ch. 5 – Spectroscopy

DAT Organic Chemistry Outline

Quiz 5.2 – UV Vis and Mass Spectrometry 1. UV spectroscopy is most useful for detecting: A. Cumulated dienes B. Carboxylic acids and amides C. Conjugated alkenes D. Esters 2. In mass spectrometry, peak abundances are measured relative to the: A. M peak B. Parent peak C. Smallest peak D. Largest peak 3. Mass spectrometry separates fragments according to: A. mass B. mass-to-charge ratio C. size D. shape 4. Which of these compounds would most likely show a base peak at m/z = 43?

5. The key fragment at m/z = 45 corresponds which of the following fragments?

6. A compound is analyzed by mass spectrometry. Its base peak at m/z = 81 comes from the most stable fragment. Which of the following is it?

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Ch. 5 – Spectroscopy

DAT Organic Chemistry Outline

Quiz 5.3 – Degrees of Unsaturation 1. How many degrees of unsaturation does the following formula have: C3H6O?

2. How many degrees of unsaturation does the following formula have: C2H6O2?

3. How many degrees of unsaturation does the following formula have: C4H2O2?

4. How many degrees of unsaturation does the following formula have: C4H4O2?

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Ch. 5 – Spectroscopy

DAT Organic Chemistry Outline

Quiz 5.4 – 13C-NMR Spectroscopy 1. How many different kinds of carbon atoms are there in the following molecules?

2. For each pair below, which of the two pink-colored carbon atoms in each pair is more positively charged (and hence, will appear further to the left by NMR)?

3. Predict what the 13C-NMR spectrum should look like for each of the following molecules:

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Ch. 5 – Spectroscopy

DAT Organic Chemistry Outline

Quiz 5.5 – 1H-NMR Spectroscopy 1. How many different kinds of hydrogen atoms are there in the following molecules?

2. For each pair below, which of the sets of pink-colored hydrogen atoms in each pair is more positively-charged (and hence, will appear further to the left by NMR)?

3. Predict what the 1H-NMR spectrum should look like for each of the following molecules.

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Ch. 5 – Spectroscopy

DAT Organic Chemistry Outline

Quiz 5.6 – Spectroscopy Analysis *Note: You likely will not see anything this hard on the DAT, but if you can answer these questions, you’ll be ready to answer anything spectroscopy related on the DAT. 1. Identify the compound that gives the following spectra. (Formula: C6H12O)

2. Identify the compound that gives the following spectra. (Formula: C6H12O2)

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Ch. 5 – Spectroscopy

DAT Organic Chemistry Outline

Quiz 5.6 – Spectroscopy Analysis (Continued) 3. Identify the compound that gives the following spectra. (Formula: C5H12O)

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