Chapter 10 Acid-Base Reactions of π-Bonds

Hydrofluoric acid can react with alkenes, but much slower than the reaction of HCl, HBr or HI Indeed, hydrogen iodide reacts rapidly with alkenes, as will HBr and HCl. Although strong acids such as HCl or HBr react with alkenes, weak acids such as water and alcohols do not react directly with alkenes. Carbocations, however, are highly reactive intermediates, and once generated they easily react with weak nucleophiles such as water or alcohols. If an alkene reacts with an acid catalyst in an aqueous medium the product is an alcohol, but in an alcohol medium the product is an ether. The reaction of cyclohexene and methanol in the presence of an acid catalyst initially gives the expected carbocation. Elemental fluorine was thought to be too reactive and too dangerous for reaction with alkenes.

Carbocation Stability

Alkenes are Br!'lnsted-Lowry Bases

Regioselectivity

Other Acids React with Alkenes

Carbocation Rearrangements

Hydration Reactions

Dihalogenation

Diastereoselective Dihalogenation

Alkenes with Hypohalous Acids

Hydroboration

Oxidation of Boranes to Alcohols

Oxymercuration-Demercuration

Alkynes With HX

Hydration and Hydroboration of Alkynes

Dihalogenation of Alkynes

Alkenes React with HBr and Radicals

Alkene Polymerization

Alkene Metathesis

Pinacol Rearrangement

Polymerization