Schmidt Reaction

The video tutorial by Professor Dave explains the importance of functional group interconversion in organic synthesis, focusing on the Curtius and Schmidt reactions. The Curtius rearrangement involves converting an acid chloride to an acyl azide, which decomposes to form an isocyanate. The Schmidt reaction, introduced by Karl Friedrich Schmidt, involves hydrazoic acid reacting with ketones to yield amides. Two mechanisms, the Baeyer-Villiger and Beckmann pathways, are discussed, highlighting selectivity issues in non-symmetrical ketones. Recent developments show alkyl azides undergoing similar reactions, with applications in synthesizing natural products.

What is the primary purpose of functional group interconversion in organic synthesis?

• To increase the molecular weight of compounds

• To transform functional groups into more reactive forms

• To convert cheap substrates into complex molecules

• To reduce the number of steps in a synthesis

Which chemist is credited with first describing the Curtius rearrangement?

• Theodor Curtius

• Jeff Aubé

• Baeyer-Villiger

• Karl Friedrich Schmidt

What is the key intermediate formed in the Schmidt reaction when reacting hydrazoic acid with ketones?

• Nitrillium cation

• Acyl azide

• Isocyanate

• Diazoiminium ion

In the Beckmann pathway, what influences the selectivity of alkyl migration?

• The temperature of the reaction

• The presence of a catalyst

• The type of solvent used

• The size of the alkyl group

Under what conditions do alkyl azides undergo the same reaction as hydrazoic acid?

• Basic conditions

• Acidic conditions

• High temperature

• Neutral conditions

What is the role of the Lewis acid in the synthesis of stenine?

• To provide a source of nitrogen

• To increase the reaction temperature

• To catalyze both the Diels-Alder and Schmidt reactions

• To act as a solvent

What is the advantage of combining the Diels-Alder reaction with the Schmidt reaction in one pot?

• It reduces the cost of synthesis

• It allows for the formation of more by-products

• It ensures the correct stereochemistry and molecular structure

• It increases the reaction time