Chapter 14.3, Problem 14.17P

Interpretation Introduction

Interpretation:

The products that is expected to be formed when the given compound is heated with excess $\text{HBr}$ has to be drawn.

Concept Introduction:

Ether are compounds that contain an oxygen atom that is sandwiched between two R groups.  The R groups may be alkyl, vinyl or aryl.

Ethers generally don’t react under mildly acidic or basic conditions.  Under a strong acidic conditions, the $\text{C}-\text{O}$ bonds can undergo cleavage.  When the ether is treated with hydrogen halides, the $\text{C}-\text{O}$ bond undergo acidic cleavage to form two alkyl halides.  The general reaction scheme can be given as,

The two alkyl groups are cleaved and alkyl halide is formed as shown above.  In this ether reaction with excess hydrogen halide, few exceptions are there.  The $\text{C}-\text{O}$ bonds that has a $s{p}^2$ hybridized center cannot be cleaved.  The general scheme can be shown as,