Wolff-Kishner Reduction

The video tutorial explains the Wolff-Kishner reduction, a method to reduce aldehydes and ketones to alkanes under basic conditions. It covers the reaction mechanism, involving hydrazine and a strong base, and highlights its applications in pharmaceutical synthesis. The tutorial also discusses modifications for milder conditions and complex strategies in organic synthesis, such as pyrrole alkylation. The Wolff-Kishner reduction remains a vital tool for organic chemists.

What is the main difference between Clemmensen and Wolff-Kishner reductions?

• Clemmensen uses acidic conditions, Wolff-Kishner uses basic conditions.

• Both use basic conditions.

• Clemmensen uses basic conditions, Wolff-Kishner uses acidic conditions.

• Both use acidic conditions.

Which chemists independently developed the Wolff-Kishner Reduction?

• Ludwig Wolff and Nikolai Kischner

• Donald Cram and Nikolai Kischner

• Nikolai Kischner and Clemmensen

• Ludwig Wolff and Donald Cram

What is the first step in the Wolff-Kishner Reduction mechanism?

• Protonation by the conjugate acid

• Formation of a carbanion

• Loss of nitrogen gas

• Formation of a hydrazone

Why is liquid hydrazine considered hazardous in the Wolff-Kishner Reduction?

• It detonates in the gas phase even without oxygen.

• It is highly acidic.

• It reacts violently with water.

• It is unstable at low temperatures.

What modification allows the Wolff-Kishner Reduction to be performed at room temperature?

• Using potassium tert-butoxide and dimethyl sulfoxide

• Using zinc and hydrochloric acid

• Using ethylene glycol and potassium hydroxide

• Using diethylene glycol and hydrazine

In the complex strategy involving pyrrole, what is the role of the thioester group?

• It facilitates alkylation at multiple positions.

• It directs acylation to a specific position.

• It prevents the reaction from occurring.

• It acts as a catalyst for the reaction.

What is the final product of the three-step procedure involving Wolff-Kishner Reduction and pyrrole?

• Pyrrole 2-carboxylate

• 2-carboxylic acid

• Dialkylated pyrrole

• 3-alkyl pyrrole