Chapter 11, Problem 11.10P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the given reaction is to be drawn, and the products for the reaction are to be predicted.

Concept introduction:

An electrophile is an electron deficient species that is attacked by a nucleophile, which is an electron-rich species. Alkenes can undergo acid-catalyzed alkoxilation reactions in which the alkenes are treated with alcohols in the presence of strong acids. The first step for these reactions is the electrophilic addition step, in which protonation of the double bond occurs. The strong acid protonates the carbon atom in the double bond so as to form the stable carbocation. Thus, the proton gets attached to the carbon atom in the alkene, which is least substituted or has greater number of hydrogen atoms attached. In step two, the oxygen atom in another molecule of alcohol serves as a base and deprotonates the oxygen atom in the alkoxy group. This results in an uncharged product.