Chapter 5, Problem 37P

Interpretation Introduction

Interpretation:

An alcohol from given alcohols, which is converted to the corresponding chloride at the fastest rate, on reaction with concentrated hydrochloric acid is to be determined. Which one reacts at the slowest rate is to be determined as well.

Concept Introduction:

The rate of reaction of alcohols with hydrogen chloride increase in the order of primary < secondary < tertiary. This is consistent with the stability of carbocation intermediates.

When a tertiary alcohol reacts with hydrogen chloride, a tertiary carbocation is formed.

When a secondary alcohol reacts with hydrogen chloride, a secondary carbocation is formed.

When a primary alcohol reacts with hydrogen chloride, a primary carbocation is formed.

Tertiary alcohols react fastest while primary alcohols react the slowest on reaction with concentrated hydrochloric acid.

More stable carbocations are formed faster, than less stable carbocations. Thus, tertiary carbocations react the fastest, while primary carbocations react the slowest on reaction with concentrated hydrochloric acid.