Midterm Preparation

Topics:
1) synthesis of 1,3-dicarbonyl (C-C bond)
2) synthesis of -hydroxycarbonyl and α,-unsaturated carbonyl (C-C bond)
3) synthesis of 1,5-dicarbonyl (C-C bond)
4) synthesis of rings via intramolecular alkylation, aldol, Claisen, and Robinson (C-C bond)
5) alkylation via α-alkylation and Gilman (C-C bond)
6) Wittig olefination (C=C bond)

Question 1: Aldol reactions. Write the products of the following aldol reactions?

Question 1: 1,2- and 1,4-Addition. Write the product of each step of the following reactions?

Question 3: Retrosynthesis () and Synthesis (). How to synthesize the compounds I–VI
using the indicated reactions? Show your retrosynthesis.
Question 4: 1,3- and 1,5-difunctional retrosynthesis models. Disconnect the target molecules to
deduce starting materials in the synthesis of the following molecules?

Question 5: Complete the synthesis sequences?

Question 6: Perform retrosynthesis and synthesis of the compound using aldol reaction?

Question 7: Perform retrosynthesis and synthesis of the compound using enolate chemistry?

Question 8: Perform retrosynthesis and synthesis of the compound using aldol reaction?

Question 9: Perform retrosynthesis and synthesis of the compound using Claisen condensation?
Question 10: Perform retrosynthesis and synthesis of the compound using aldol condensation,
Wittig olefination, and 1,4-addition?

Question 11: Perform retrosynthesis and synthesis of the compound using carbonyl addition of
organometallics?

Question 12: Perform retrosynthesis and synthesis of the compound using aldol condensation
and Wittig olefination?

Question 13: Complete the synthesis route of the following compound?

Exam structure: 1) 60% theoretical problems (Power point, instructions, review problems)
2) 20% multiple synthesis
3) 20% retrosynthesis and synthesis