Chapter 14, Problem 45PP

Interpretation Introduction

Interpretation: The unknown compound B to be identified.

Concept Introduction:

Acidic cleavage of Ethers: Generally ethers are unreactive under basic or mildly acidic conditions. When the ethers are heated with a concentrated solution of a strong acid, ether will undergo acidic cleavage in which ether is converted into two alkyl halides.

$\text{HBr \&}\text{HI}$ Acids are used to cleave ether. $\text{HCl}$ Is less effective, but $\text{HF}$ acid does not cleave ethers due to the relative nucleophilicity of the halide ions.

Two step mechanistic ways:

1. I. Proton transfer.
2. II. Nucleophile attack via ${\text{S}}_{\text{N}}\text{2}$ process.

HDI Calculation:

$\begin{array}{l}\text{HDI=}\frac{\text{2(C)+2+N-H-X}}{\text{2}}\\ \text{where,}\\ \text{C}\text{represent}\text{number}\text{of}\text{carbons}\text{.}\\ \text{N}\text{represent}\text{number}\text{of}\text{Nitrogens}\text{.}\\ \text{H}\text{represent}\text{number}\text{of}\text{Hydrogens}\text{.}\\ \text{X}\text{represent}\text{number}\text{of}\text{Halogens}\text{.}\end{array}$

To Identify: The unknown compound B to be identified.