Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

The following is not an appropriate reaction for the preparation of t-butyl ethyl ether because:

Options:

Sodium ethoxide is a weak base

Alkyl halide is tertiary in nature

Sodium ethoxide is a strong base

The ether formed is very bulky

Correct Answer:

Sodium ethoxide is a strong base

Explanation:

The following is not an appropriate reaction for the preparation of t-butyl ethyl ether because sodium ethoxide is a strong base.

Sodium ethoxide is a strong base and will deprotonate the tertiary carbon atom of t-butyl chloride, forming the t-butyl carbocation. The t-butyl carbocation is a very unstable carbocation and will rearrange to form the more stable isobutyl carbocation. The isobutyl carbocation will then react with the ethoxide ion to form isobutyl ethyl ether.

Therefore, the correct answer is 3. Sodium ethoxide is a strong base.

The other options are incorrect:

  • Alkyl halides can be primary, secondary, or tertiary in nature. The nature of the alkyl halide does not affect the outcome of the reaction.
  • The ether formed is not very bulky. t-Butyl ethyl ether is a relatively small ether