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.

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What is the mechanism of the Claisen condensation?

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What is known as the Claisen condensation?

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What is the mechanism of the Dieckmann Condensation?

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