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Organic
Chemistry III
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Professor
Carl C. Wamser
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Chapter
20 Homework
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1. Write a complete mechanism for a directed aldol condensation between
cyclohexanone (as the enolate) and pentanal.
2. Number the carbons in 2,6-heptanedione and then apply the same numbers
to identify the carbons in each of two possible intramolecular aldol products
(after dehydration). Indicate which would be expected to be the major product.
3. Write a complete mechanism for the NaOH-catalyzed aldol reaction of
cyclopentanone, including dehydration.
1. Condensation reactions seem
to have developed more "name" reactions
than most other areas of organic chemistry. For each reaction below, identify
the alpha-nucleophile and the carbonyl
group that would have been involved.
a) Perkin condensation
b) Knoevenagel condensation
c) Dieckmann condensation
2. Write a complete mechanism for a mixed Claisen condensation between
ethyl acetate and ethyl benzoate, using sodium ethoxide as the base.
