Chapter 17 (Aldehydes and Ketones: Nucleophilic Addition to the

Chapter 17 (Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group)
Nucleophilic vs. Electrophilic attack
Alkyl groups stabilize reactants (electronic) and crowd product (steric)
Table 17.3 Equilibrium Constants and Relative Rates of Hydration
Synthetic Strategy
1. Protect C=O
2. Alkylate
3. Restore C=O
Stereospecificity of carbonyl additions (slide 40)
Chapter 18 (Enols and Enolates)
Greek letter assignments
Acidity of α-Hydrogen
Table 18.1 pKa Values of Some Aldehydes and Ketones
Intramolecular aldol condensation
Mixed aldol condensations (will be on test)
To carry out a mixed aldol condensation:
1. Choose component that cannot form an enolate (slide 24)
2. OR use a very strong/non-nucleophilic base (slide 25)
Enol Stability (slides 29-30)
Stereochemistry (slides 34-36)
Conjugation (slides 37-44)
Strongly basic nucleophiles: Grignard reagents, LiAlH4, NaBH4, sodium acetylide
strongly basic nucleophiles add irreversibly
Weakly basic nucleophiles: cyanide ion (CN-), thiolate ions (RS-), ammonia and amines, azide ion (N3-)
weakly basic nucleophiles add reversibly