Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

Choose the correct statement(s) for intermolecular dehydration of alcohols to form ethers

(A)The formation of ether may involve a nucleophilic bimolecular $SN^2$ reaction or $SN^1$ reaction
(B) The method is successful with secondary and tertiary alcohols.
(C) The reaction requires protic acids
(D) The reaction is carried out at low temperature.

Choose the correct answer from the options given below:

Options:

(A), (B) and (D) only

(A), (C) and (D) only

(A), (B), (C) and (D)

(B), (C) and (D) only

Correct Answer:

(A), (C) and (D) only

Explanation:

The correct answer is Option (2) → (A), (C) and (D) only

Detailed Analysis of Statements

  • (A) The formation of ether may involve an $S_N2$ or $S_N1$ reaction: This is correct. While the dehydration of primary alcohols (like ethanol) typically follows the $S_N2$ pathway, secondary or tertiary alcohols (though less efficient) tend to follow the $S_N1$ pathway via a carbocation intermediate.
  • (B) The method is successful with secondary and tertiary alcohols: This is incorrect. This method is primarily successful for primary alcohols. In the case of secondary and tertiary alcohols, the elimination reaction (dehydration to form an alkene) competes strongly with substitution. Steric hindrance in tertiary alcohols makes the $S_N2$ attack of another alcohol molecule nearly impossible, leading almost exclusively to alkenes.
  • (C) The reaction requires protic acids: This is correct. The reaction is catalyzed by concentrated protic acids such as $H_2SO_4$ or $H_3PO_4$. The acid is necessary to protonate the $-OH$ group, converting it into a good leaving group ($-H_2O^+$).
  • (D) The reaction is carried out at low temperature: This is correct (relative to alkene formation). Temperature control is critical. For example, the dehydration of ethanol:
    • At 413 K (140°C), the major product is diethyl ether (substitution).
    • At 443 K (170°C), the major product is ethene (elimination).