Chapter 13, Problem 13.29E

What products would result from the following processes?

Write an equation for each reaction.

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

b. $1$-Butanol is subjected to an excess of oxidizing agent.

c. $2$-Pentanol is subjected to controlled oxidation.

d. $2$-Pentanol is heated to $180°\text{C}$ in the presence of sulfuric acid.

e. $2$-Methyl- $2$-pentanol is subjected to controlled oxidation.

Interpretation Introduction

(a)

Interpretation:

The product formed when $1$-Butanol 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 13.29E

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

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

Interpretation Introduction

(b)

Interpretation:

The product formed by the excess oxidation of $1$-Butanol 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 13.29E

The product formed by the excess oxidation of $1$-Butanol is shown below.

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 primary alcohol, $1-$ butanol on oxidation gives butyric acid as shown below.

Figure 2

Conclusion

The product formed by the excess oxidation of $1$-Butanol is shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The product formed by the controlled oxidation of $2$-Pentanol 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 13.29E

The product formed when $2$-Pentanol is subjected to controlled oxidation is shown below.

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 compound $2$-Pentanol is a secondary alcohol. Therefore, the oxidation of $2$-Pentanol gives ketone. The reaction is shown below.

Figure 3

Conclusion

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

Interpretation Introduction

(d)

Interpretation:

The product formed when $2$-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 13.29E

The product formed when $2$-Pentanol is heated to $180°\text{C}$ in the presence of sulfuric acid is shown below.

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 4

Conclusion

Interpretation:

The product formed when $2$-Pentanol is heated to $180°\text{C}$ in the presence of sulfuric acid is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The product formed by the controlled oxidation of $2$-methyl-$2$-pentanol 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 13.29E

No product is formed by the controlled oxidation of $2$-methyl-$2$-pentanol.

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-$2$-pentanol gives no product because $2$-methyl-$2$-pentanol is a tertiary alcohol.

Conclusion

No product is formed by the controlled oxidation of $2$-methyl-$2$-pentanol.