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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

Which of the following does not give nucleophilic substitution with alcohol?

A

CH₃COCl

B

Acetic anhydride

C

Ether

D

None of the above

Step-by-Step Solution

Alcohols (ROHR-OH) act as nucleophiles due to the presence of lone pairs on the oxygen atom. They undergo nucleophilic acyl substitution reactions with acid derivatives like Acid Chlorides (CH3COClCH_3COCl) and Acid Anhydrides ((CH3CO)2O(CH_3CO)_2O) to form esters.

  1. With CH3COClCH_3COCl: ROH+CH3COClCH3COOR+HClR-OH + CH_3COCl \rightarrow CH_3COOR + HCl (Vigorous reaction).
  2. With Acetic Anhydride: ROH+(CH3CO)2OCH3COOR+CH3COOHR-OH + (CH_3CO)_2O \rightarrow CH_3COOR + CH_3COOH (Reaction occurs in presence of acid/base).
  3. With Ether: Ethers (RORR-O-R') are quite stable towards nucleophilic attack because the alkoxide ion (RORO^-) is a poor leaving group. Therefore, alcohols do not react with ethers via nucleophilic substitution under standard conditions.

Thus, Ether is the compound that does not give nucleophilic substitution with alcohol.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersfollowingnucleophilicsubstitutionalcohol

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