Organic Chemistry II

Professor Carl C. Wamser

Chem 335 - Winter 2006

Chapter 18 Homework Answers

Carey, pages 814 - 821 :
Problems 18.22 - 44

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.