Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

Read the passage carefully and answer the questions.

Replacement of a hydrogen atom in a hydrocarbon by an alkoxy or carboxyl group yields a class of compounds known as ethers. Ethers are classified as symmetrical or unsymmetrical on the basis of groups attached to the oxygen atoms. Diethyl ether, a symmetrical ether, has been widely used as an inhalation anesthetic. Ethers can be prepared by acid catalyzed intermolecular dehydration of alcohols and Williamson's synthesis. Acid catalyzed dehydration of alcohols is not generally preferred as it gives a mixture of elimination and substitution products. In Williamson's synthesis, an alkyl halide is allowed to react with sodium alkoxide. Ethers containing substituted Alkyl groups may also be prepared by this method. The C-O bond in ether is weakly polar and is cleaved under drastic conditions with excess of hydrogen halides. In electrophilic substitution, the alkoxy group deactivates the aromatic ring and directs the incoming group to ortho and para positions.

When ethanol is dehydrated in the presence of $H_2SO_4$ at 443 K and 413 K respectively the products formed are

Options:

Ethane and ethoxythane

Ethylmethyl ether and butene

Ethylmethyl ether and propene

Ethene and ethoxyethane

Correct Answer:

Ethene and ethoxyethane

Explanation:

The correct answer is Option (4) → Ethene and ethoxyethane

The outcome of the dehydration of ethanol with sulfuric acid ($\text{H}_2\text{SO}_4$) is highly dependent on the temperature at which the reaction is carried out.

1. At 443 K (Higher Temperature)

At this temperature, intra-molecular dehydration occurs. A molecule of water is removed from a single molecule of ethanol, leading to the formation of a double bond.

  • Process: Elimination reaction.
  • Product: Ethene ($\text{CH}_2=\text{CH}_2$).

2. At 413 K (Lower Temperature)

At this lower temperature, inter-molecular dehydration occurs. One molecule of water is removed from between two molecules of ethanol.

  • Process: Nucleophilic substitution reaction ($\text{S}_{\text{N}}2$).
  • Product: Ethoxyethane (Diethyl ether, $\text{C}_2\text{H}_5-\text{O}-\text{C}_2\text{H}_5$).