Chapter 14, Problem 14.62EP

Interpretation Introduction

Interpretation:

Why 2-ethyl-2-methyl-1-butanol cannot be dehydrated has to be explained.

Concept Introduction:

Dehydration reaction is the loss of water from a single reactant.  Alcohol undergoes dehydration reaction to form alkene.  Sulfuric acid acts as a catalyst for hydration of alkene at room temperature.  The same sulfuric acid acts as a dehydrating agent when treated with alcohol at high temperature.  If the reaction is carried out at a lower temperature, the loss of water molecule takes place from two molecule of reactant.  This results in the formation of ether.  Primary alcohol when treated with sulfuric acid at lower temperature ($\text{140}\text{°C}$) gives ether as the product while secondary and primary alcohol gives alkene as the main product in good yield.