Organic Chemistry 1: Alkyne Reactions and Tautomerization

Vocabulary flashcards covering alkyne halogenation, acid-catalyzed hydration with sulfuric acid and hydronium, and keto-enol tautomerization mechanisms.

Enol

An intermediate structure containing a hydroxyl group directly attached to an alkene carbon ($\text{C}=\text{C}-\text{OH}$), formed during the acid-catalyzed hydration of an alkyne prior to tautomerizing into a ketone.

Keto-enol tautomerization

The acid-catalyzed isomerization process through which an enol intermediate converts into a more stable carbonyl compound (ketone).

Acid-catalyzed alkyne hydration

A reaction where an alkyne reacts with $\text{H}_2\text{SO}_4$ and $\text{H}_2\text{O}$ (generating $\text{H}_3\text{O}^+$) to add water across the triple bond, yielding a ketone via an enol intermediate.

Geminal dichloride

A molecule bearing two chlorine atoms bonded to the identical carbon atom, produced through the addition of hydrogen chloride across an alkyne via a carbocation intermediate.

Tetrahalogenation of alkynes

The complete halogen addition across a carbon-carbon triple bond yielding a product with four chlorine atoms bound to adjacent carbons (a tetrachloroalkane).

Carboanion

A carbon species bearing a lone pair of electrons and a negative charge, identified in the lecture mechanism as an intermediate during the tautomerization sequence.