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Name:
Organic Chemistry - CHEM 231B
Test # February 27, 2002
- Provide answers to the following questions: (32 points)
1a. Briefly explain the fundamental principles of IR spectroscopy. (8 points)
1b. What are organometallic reagents? Provide two examples and explain their reactivity.(8 points)
1c. What information can we get from 13 C NMR spectrometry? (8 points)
1d. In organic chemistry, when we talk about oxidation and/or reduction, what are we talking about? Provide examples as needed. (8 points)
- Predict products or reagents for the following reactions and briefly explain your answer. (5 @ 8 pts = 40 points)
2a.
2b.
2c.
2d.
2e.
H
O
Br
- Mg / Et 2 O
- Work-up with mild acid IR Spectra for both compounds have an absorbance at 3250 cm-1and have very similar though not identical fingerprint region
Product 2b and Product 2c
HO
Br ?
H
O
Br
- TosCl / Pyridine
- Potassium t-butoxide
Product 2b Product 2d
- TosCl / Pyridine
- Potassium t-butoxide
Product 2c Product 2e
Product 2d and 2e
- Consider the following problem: (26 points)
O Make this
From any alkane with four or less carbons
4a. Conduct a retrosynthetic analysis for the above problem. Investigate more than one method to make the desired molecule; the various methods do not have to be completely correct, but rather should show that you have thought of alternative routes. (13 points)
4b. Using the best approach from problem 4a, synthesize the desired molecule. Mechanisms are not required, but reagents and conditions are required. (13 points)
