Chapter 11, Problem 11.17P

(a)

Interpretation Introduction

Interpretation:

The structural formula for the product formed when given compound is heated at reflux in con. $\text{HI}$ has to be drawn.

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

(b)

Interpretation Introduction

Interpretation:

The structural formula for the product formed when given compound is heated at reflux in con. $\text{HI}$ has to be drawn.

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

(c)

Interpretation Introduction

Interpretation:

The structural formula for the product formed when given compound is heated at reflux in con. $\text{HI}$ has to be drawn.

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

(d)

Interpretation Introduction

Interpretation:

The structural formula for the product formed when given compound is heated at reflux in con. $\text{HI}$ has to be drawn.

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