Chapter 13, Problem 13.28E

What products would result from the following processes?

Write an equation for each reaction.

a. $2$-Methyl- $2$-butanol is subjected to controlled oxidation.

b. $1$-Propanol is heated to $140°\text{C}$ in the presence of sulfuric acid.

c. $3$-Pentanol is subjected to controlled oxidation.

d. $3$-Pentanol is heated to $180°\text{C}$ in the presence of sulfuric acid.

e. $1$-Hexanol is subjected to an excess of oxidizing agent.

Interpretation Introduction

(a)

Interpretation:

The product formed when $2$-Methyl-$2$-butanol is subjected to controlled oxidation is to be drawn.

Concept introduction:

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

Answer to Problem 13.28E

No product is formed when $2$-Methyl-$2$-butanol is subjected to controlled oxidation.

Explanation of Solution

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

The controlled oxidation of $2$-Methyl-$2$-butanol gives no product because $2$-Methyl-$2$-butanol is a tertiary alcohol.

Conclusion

No product is formed when $2$-Methyl-$2$-butanol is subjected to controlled oxidation.

Interpretation Introduction

(b)

Interpretation:

The product formed when $1$-Propanol is heated to $140°\text{C}$ in the presence of sulfuric acid is to be drawn.

Concept introduction:

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

Answer to Problem 13.28E

The product formed when $1$-Propanol is heated to $140°\text{C}$ in the presence of sulfuric acid is,

Explanation of Solution

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

Alcohols on heating at temperature $140°\text{C}$ in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ give ether. The reaction is shown below,

Figure 1

Conclusion

The product formed when $1$-Propanol is heated to $140°\text{C}$ in the presence of sulfuric acid is shown in Figure 1.

Interpretation Introduction

(c)

Interpretation:

The product formed when $3$-Pentanol is subjected to controlled oxidation is to be drawn.

Concept introduction:

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

Answer to Problem 13.28E

The product formed when $3$-Pentanol is subjected to controlled oxidation is,

Explanation of Solution

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

As $3$-Pentanol is a secondary alcohol the oxidation of $3$-Pentanol gives ketone. The reaction is shown below,

Figure 2

Conclusion

The product formed when $3$-Pentanol is subjected to controlled oxidation is shown in Figure 2.

Interpretation Introduction

(d)

Interpretation:

The product formed when $3$-Pentanol is heated to $180°\text{C}$ in the presence of sulfuric acid is to be drawn.

Concept introduction:

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

Answer to Problem 13.28E

The product formed when $3$-Pentanol is heated to $180°\text{C}$ in the presence of sulfuric acid is,

Explanation of Solution

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

Alcohols on heating at temperature $180°\text{C}$ in the presence of ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$ undergo dehydration and give alkene. The reaction is shown below.

Figure 3

Conclusion

The product formed when $3$-Pentanol is heated to $180°\text{C}$ in the presence of sulfuric acid is shown in Figure 3.

Interpretation Introduction

(e)

Interpretation:

The product formed when $1$-Hexanol is subjected to an excess of oxidizing agent is to be drawn.

Concept introduction:

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

Answer to Problem 13.28E

The product formed when $1$-Hexanol is subjected to an excess of oxidizing agent is,

Explanation of Solution

Ketones can be prepared by the oxidation reaction of secondary alcohol. On the other hand, primary alcohols on oxidation with weak oxidant give aldehyde and with strong oxidant give carboxylic acid. No product is obtained by the oxidation of tertiary alcohol.

Generally, primary alcohols on oxidation give aldehyde. However, in the presence of excess oxidizing agent, aldehyde further oxidizes to carboxylic acid. Therefore, the product formed when $1$-Hexanol is subjected to an excess of oxidizing agent is,

Figure 4

Conclusion

The product formed when $1$-Hexanol is subjected to an excess of oxidizing agent is shown in Figure 4.