Chapter 10, Problem 10.41AP

Interpretation Introduction

(a)

Interpretation:

The structure of seven-carbon tertiary alcohol which yields a single alkene after acid-catalyzed dehydration is to be stated.

Concept introduction:

The dehydration of alcohol in the presence of acid catalyst results in the formation of an alkene with the removal of one molecule of water. Dehydration of alcohol is a type of $\text{β-}$ elimination reaction, in which beta hydrogen is eliminated from the alcohol molecule. If all beta hydrogen in alcohol is equivalent, then only single alkene will be the major product.

Interpretation Introduction

(b)

Interpretation:

The structure of alcohol that, after acid-catalyzed dehydration yields an alkene and after the ozonolysis followed with ${\left({\text{CH}}_{\text{3}}\right)}_2\text{S}$, gives only benzaldehyde is to be stated.

Concept introduction:

The dehydration of alcohol in the presence of acid catalyst results in the formation of an alkene with the removal of one molecule of water. Dehydration of alcohol is a type of $\text{β-}$ elimination reaction, in which beta hydrogen is eliminated from the alcohol molecule. If all beta hydrogen in alcohol is equivalent, then only single alkene will be the major product.

Interpretation Introduction

(c)

Interpretation:

The structure of alcohol that gives the same product when it reacts with ${\text{KMnO}}_{\text{4}}$ as it obtained from the ozonolysis of $trans-3,6-\text{dimethyl}-4-\text{octene}$ followed by treatment with $\text{H}{\text{2}}_{}{\text{O}}_{\text{2}}$ is to be stated.

Concept introduction:

Potassium permanganate $\left({\text{KMnO}}_{\text{4}}\right)$ is a useful oxidizing agent, which can oxidize primary alcohol to carboxylic acid in the presence of basic solution but not used in secondary alcohol to ketones because ketones react further with alkaline permanganate solution. The oxidative ozonolysis of alkene also produces a carboxylic acid.