Principles of Organic Synthesis

What is the base catalyzed carbon-carbon bond formation closely related to?

• Formation from organometallic reagents

• Formation from alkyl halides

• Formation from alcohols

• Formation from carboxylic acids

What factors does the scope of base-catalyzed reactions depend on?

• The ability to form carbanions

• The type of electrophilic carbon

• The temperature of the reaction

• The presence of a solvent

What is the reaction that has become one of the most important methods for carbon-carbon bond formation?

• Aldol Condensation

• Michael Addition

• Claisen Condensation

• Friedel-Crafts Reaction

What determines the product distribution under thermodynamic control?

• Relative stabilities of six-membered chair-shaped cyclic transition states

• The size of the substituents

• The type of base used

• The temperature of the reaction

What can be used to increase the degree of diastereoselectivity?

• Converting enolate into silyl enol ethers

• Using a stronger base

• Increasing the temperature

• Using a different solvent

What has been well explored in the asymmetric version of the aldol reaction?

• Chiral auxiliaries and chiral catalysts

• Different solvents

• Temperature variations

• Different bases

What products would you expect from the following reactions? Provide mechanism.

What is the mechanism of the Claisen condensation?

What is known as the Claisen condensation?

What is the mechanism of the Dieckmann Condensation?