Chem 275 Practice Problem Set – Friday, October 29, 2010 – J. Magolan
This problem set includes questions covering material from chapters 7, 8 and 9 in your textbook.
1. Name the following commpounds.
2. Draw the appropriate curly arrows to complete these transformations:
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Chem 275 Practice Problem Set – Friday, October 29, 2010 – J. Magolan
3. Draw the product of these reactions.
4. Draw the mechanism of this reaction. (Include all four major resonance contributors of the cationic
intermediate)
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Chem 275 Practice Problem Set – Friday, October 29, 2010 – J. Magolan
5. What product(s) would you expect from these reactions:
6.
Draw the mechanism and expected product of this reaction:
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Chem 275 Practice Problem Set – Friday, October 29, 2010 – J. Magolan
7.
Draw the expected products:
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Chem 275 Practice Problem Set – Friday, October 29, 2010 – J. Magolan
8. Draw the expected products:
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Chem 275 Practice Problem Set – Friday, October 29, 2010 – J. Magolan
9. Draw the complete arrow pushing mechanism for the formation of this hemi-acetal.
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Chem 275 Practice Problem Set – Friday, November 5, 2010 – J. Magolan
This problem set focuses mainly on chapters 13, 14 and 15 or your text.
1. Name the following compounds.
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Chem 275 Practice Problem Set – Friday, November 5, 2010 – J. Magolan
2. Indicate the product of the following reactions
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Chem 275 Practice Problem Set – Friday, November 5, 2010 – J. Magolan
3. Complete the following mechanisms
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Chem 275 Practice Problem Set – Friday, November 5, 2010 – J. Magolan
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4. Explain why this occurs:
5. The structure below is an unstable compound. If you made it, it would rapidly react to form something
different. What would that be? Draw the complete mechanism for the process.
Chem 275 Practice Problem Set – Friday, November 12, 2010 – J. Magolan
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This problem set focuses mainly on chapters 15 and 16 of your text.
1. Draw an example of each of the following:
a. aldehyde
b. ketone
c. carboxylic acid
d. ester
e. amide
f. acid chloride
g. anhydride
h. amine
i. imine
j. ammonium
k. iminium
l. enol
m. enolate
n. α-β unsaturated ester
o. α-β unsaturated aldehyde
p. carboxylic acid with a β-carbonyl group
2. Draw example mechanisms of both acid and base catalyzed hydrolysis of an ester.
3. Show an example of LiAlH4 reduction of an acid, ester, and amide.
4. Show an example of NaBH4 reduction of a compound that has both ketone and aldehyde groups.
5. Give an example, including mechanism, of a decarboxylation reaction of a β-keto carboxylic acid.
6. Show examples of aldol, Claisen, and dieckman reactions.
7. Draw a compound that can have two different enolate anions. Show the mechanisms for the formation of
both possible enolates.
8. Show an example of an aldol reaction.
9. Show examples of Claisen and Dieckman reacitons.
10. Show an example of a Michael reaction of an amine with an α-β unsaturated ester. Give the complete
mechanism.